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Table numbers are rounded to 7 significant digits; decoded details retain full precision.
Swarm intelligence for chemical reaction optimisation (Schlama et al.): Pd-catalysed sulfonamide coupling and Suzuki coupling HTE campaigns
Dataset description
High-throughput experimentation (HTE) data from R. Schlama, J. W. Sin, R. P. Burwood, K. Püntener, R. Bigler and P. Schwaller, "Swarm Intelligence for Chemical Reaction Optimisation", arXiv:2509.11798 (2025), doi:10.48550/arXiv.2509.11798; journal version "Swarm intelligence for chemical reaction optimization", Chem (2026), doi:10.1016/j.chempr.2026.103035. The dataset keeps the paper's two experimental HTE datasets together (989 reactions). Both were run in 1 mL vials in 96-position reaction blocks on a glove-box-enclosed Unchained Labs HTE platform: SI section and figure numbers refer to the arXiv version. (1) Pd-catalysed sulfonamide N-arylation of 1-chloro-4-methoxybenzene (10 mg, 70.1 µmol, 1.00 equiv) with benzenesulfonamide (13.8 mg, 1.25 equiv): Pd precursor (0.03 equiv), monophosphine ligand (0.03 equiv), base (2.5 equiv; or NaTFA 1.25 equiv + DBU 1.25 equiv), solvent (150 µL), 70 °C, 18 h. 585 reactions (SI section 7). The authors collected these to build a virtual benchmark on which alpha-PSO and Bayesian optimisation were compared in silico. 96 of them match the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9, as in the Suzuki configurations); the paper does not list these reactions, nor how the other 489 were chosen. (2) Pd-catalysed Suzuki-Miyaura coupling of 3-chloropicolinonitrile (72.2 µmol, 1.00 equiv) with (4,6-dimethoxypyrimidin-5-yl)boronic acid (1.25 equiv): Pd precursor (0.03 equiv), monophosphine ligand (0.03 equiv), base (2.0 equiv), solvent alone (86 reactions) or solvent plus water with SURF solvent fractions 0.75/0.25 (318 reactions; the paper gives no ratio), 70 °C, 20 h. 404 reactions (SI section 8; main-text Figure 6). The campaign started from a 96-reaction Sobol-sampled plate, followed by two optimisation iterations run in parallel by alpha-PSO and by Bayesian optimisation (qNEHVI), with 96 suggestions per method per iteration (alpha-PSO with c_local = 1.5, c_social = 0.5, c_ml = 2.0, chosen after landscape analysis of the Sobol plate; BO with qNEHVI in the Minerva workflow). Unique conditions: 96 in iteration 1, 136 new in iteration 2, 172 new in iteration 3. A condition suggested by both methods, or in both iterations, appears once. Each reaction's notes give its iteration and method, reconstructed from the authors' plate-suggestion files. The total solvent volume is not reported for this campaign and is recorded as an unmeasured amount with the volume fractions. Reactions were diluted with 4/1 MeCN/H2O (500 µL) and shaken 20 min, and a 50 µL aliquot was analysed by UPLC-MS (Waters ACQUITY UPLC I-Class with QDa). Outcomes are the authors' LC area-percent values. "AP yield" is recorded as an AREA measurement in percent: uncalibrated, with no internal standard, not a quantitative yield. "AP selectivity" is recorded as a CUSTOM SELECTIVITY measurement in percent. AP yield values of 0 are real negative results and are kept. The paper gives no formula for AP selectivity but treats AP yield above AP selectivity as physically impossible (SI section 3.1); the source files nevertheless report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions). These look like a cut-off rather than measured values and are recorded as reported. The ligand named "P(tBu)3" in both source files is recorded as PtBu3·HBF4 in the sulfonamide reactions and as free P(t-Bu)3 in the Suzuki reactions, following SI Figures 35 and 39. The precursor drawn as "[Pd(dba)3]" in SI Figures 36 and 40 is recorded as Pd2(dba)3, following the SURF files and main-text Figure 6a. Source data: the authors' SURF files pd_sulfonamide_SURF.csv and pd_suzuki_SURF.csv (github.com/schwallergroup/alphaswarm, data/HTE_datasets, commit 641b258, MIT licence). The SURF files give starting materials and products as SMILES and all other components by name. The curator added structures for the Pd precursors, ligands, bases and solvents. Each was checked three ways: against the structures the authors drew for every component in SI Figures 35/36 (sulfonamide) and 39/40 (Suzuki), against the CAS numbers the same laboratory recorded for these reagents in its companion Minerva data (github.com/schwallergroup/minerva), and against PubChem. Each reaction's notes give its source file and row. Curated for the Open Reaction Database via Tokens for Progress.
Decoded from the bound file. This is a read-only preview, not schema validation or scientific verification. Missing values remain unreported; AREA is not relabeled as YIELD.
| Location | Record | Inputs and roles | Temperature | Reported measurements | Source |
|---|---|---|---|---|---|
| reactions[0] | Record 1 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd2(dba)3] REAGENT: Na2CO3 REACTANT: benzenesulfonamide CATALYST: PPh3 SOLVENT: acetonitrile | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[0]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"details": "Labelled '[Pd(dba)3]' in SI Figures 36 and 40; recorded as Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(0)), following the SURF files and main-text Figure 6a.",
"value": "O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]"
},
{
"type": "NAME",
"value": "[Pd2(dba)3]"
},
{
"type": "NAME",
"value": "tris(dibenzylideneacetone)dipalladium(0)"
},
{
"type": "CAS_NUMBER",
"value": "51364-51-3"
},
{
"type": "PUBCHEM_CID",
"value": "9811564"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[Na+].[Na+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "Na2CO3"
},
{
"type": "NAME",
"value": "sodium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "497-19-8"
},
{
"type": "PUBCHEM_CID",
"value": "10340"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(P(c2ccccc2)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "PPh3"
},
{
"type": "NAME",
"value": "triphenylphosphine"
},
{
"type": "CAS_NUMBER",
"value": "603-35-0"
},
{
"type": "PUBCHEM_CID",
"value": "11776"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "CAS_NUMBER",
"value": "75-05-8"
},
{
"type": "PUBCHEM_CID",
"value": "6342"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 1 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[1] | Record 2 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: Na2CO3 REACTANT: benzenesulfonamide CATALYST: PPh3 SOLVENT: anisole | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[1]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[Na+].[Na+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "Na2CO3"
},
{
"type": "NAME",
"value": "sodium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "497-19-8"
},
{
"type": "PUBCHEM_CID",
"value": "10340"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(P(c2ccccc2)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "PPh3"
},
{
"type": "NAME",
"value": "triphenylphosphine"
},
{
"type": "CAS_NUMBER",
"value": "603-35-0"
},
{
"type": "PUBCHEM_CID",
"value": "11776"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccccc1"
},
{
"type": "NAME",
"value": "anisole"
},
{
"type": "CAS_NUMBER",
"value": "100-66-3"
},
{
"type": "PUBCHEM_CID",
"value": "7519"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 2 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[2] | Record 3 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: diisopropylethylamine REACTANT: benzenesulfonamide CATALYST: PPh3 SOLVENT: cyclopentyl-methyl-ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[2]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN(C(C)C)C(C)C"
},
{
"type": "NAME",
"value": "diisopropylethylamine"
},
{
"type": "NAME",
"value": "N,N-diisopropylethylamine"
},
{
"type": "CAS_NUMBER",
"value": "7087-68-5"
},
{
"type": "PUBCHEM_CID",
"value": "81531"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 2
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(P(c2ccccc2)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "PPh3"
},
{
"type": "NAME",
"value": "triphenylphosphine"
},
{
"type": "CAS_NUMBER",
"value": "603-35-0"
},
{
"type": "PUBCHEM_CID",
"value": "11776"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1CCCC1"
},
{
"type": "NAME",
"value": "cyclopentyl-methyl-ether"
},
{
"type": "NAME",
"value": "cyclopentyl methyl ether"
},
{
"type": "CAS_NUMBER",
"value": "5614-37-9"
},
{
"type": "PUBCHEM_CID",
"value": "138539"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 3 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[3] | Record 4 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(OAc)2] REAGENT: DBU REACTANT: benzenesulfonamide CATALYST: PPh3 SOLVENT: 2-methyl-2-butanol | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[3]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(OAc)2]"
},
{
"type": "NAME",
"value": "palladium(II) acetate"
},
{
"type": "CAS_NUMBER",
"value": "3375-31-3"
},
{
"type": "PUBCHEM_CID",
"value": "167845"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCC2=NCCCN2CC1"
},
{
"type": "NAME",
"value": "DBU"
},
{
"type": "NAME",
"value": "1,8-diazabicyclo[5.4.0]undec-7-ene"
},
{
"type": "CAS_NUMBER",
"value": "6674-22-2"
},
{
"type": "PUBCHEM_CID",
"value": "81184"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 2
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(P(c2ccccc2)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "PPh3"
},
{
"type": "NAME",
"value": "triphenylphosphine"
},
{
"type": "CAS_NUMBER",
"value": "603-35-0"
},
{
"type": "PUBCHEM_CID",
"value": "11776"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "2-methyl-2-butanol"
},
{
"type": "NAME",
"value": "2-methylbutan-2-ol (tert-amyl alcohol)"
},
{
"type": "CAS_NUMBER",
"value": "75-85-4"
},
{
"type": "PUBCHEM_CID",
"value": "6405"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 4 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[4] | Record 5 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(OAc)2] REAGENT: NaTFA REAGENT: DBU REACTANT: benzenesulfonamide CATALYST: P(Cy)3 SOLVENT: 2-methyl-2-butanol | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[4]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(OAc)2]"
},
{
"type": "NAME",
"value": "palladium(II) acetate"
},
{
"type": "CAS_NUMBER",
"value": "3375-31-3"
},
{
"type": "PUBCHEM_CID",
"value": "167845"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])C(F)(F)F.[Na+]"
},
{
"type": "NAME",
"value": "NaTFA"
},
{
"type": "NAME",
"value": "sodium trifluoroacetate"
},
{
"type": "CAS_NUMBER",
"value": "2923-18-4"
},
{
"type": "PUBCHEM_CID",
"value": "517019"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCC2=NCCCN2CC1"
},
{
"type": "NAME",
"value": "DBU"
},
{
"type": "NAME",
"value": "1,8-diazabicyclo[5.4.0]undec-7-ene"
},
{
"type": "CAS_NUMBER",
"value": "6674-22-2"
},
{
"type": "PUBCHEM_CID",
"value": "81184"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 2
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCC(P(C2CCCCC2)C2CCCCC2)CC1"
},
{
"type": "NAME",
"value": "P(Cy)3"
},
{
"type": "NAME",
"value": "Tricyclohexylphosphine"
},
{
"type": "CAS_NUMBER",
"value": "2622-14-2"
},
{
"type": "PUBCHEM_CID",
"value": "75806"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "2-methyl-2-butanol"
},
{
"type": "NAME",
"value": "2-methylbutan-2-ol (tert-amyl alcohol)"
},
{
"type": "CAS_NUMBER",
"value": "75-85-4"
},
{
"type": "PUBCHEM_CID",
"value": "6405"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 5 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[5] | Record 6 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd2(dba)3] REAGENT: NaTFA REAGENT: DBU REACTANT: benzenesulfonamide CATALYST: PtBu3·HBF4 SOLVENT: acetonitrile | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[5]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"details": "Labelled '[Pd(dba)3]' in SI Figures 36 and 40; recorded as Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(0)), following the SURF files and main-text Figure 6a.",
"value": "O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]"
},
{
"type": "NAME",
"value": "[Pd2(dba)3]"
},
{
"type": "NAME",
"value": "tris(dibenzylideneacetone)dipalladium(0)"
},
{
"type": "CAS_NUMBER",
"value": "51364-51-3"
},
{
"type": "PUBCHEM_CID",
"value": "9811564"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])C(F)(F)F.[Na+]"
},
{
"type": "NAME",
"value": "NaTFA"
},
{
"type": "NAME",
"value": "sodium trifluoroacetate"
},
{
"type": "CAS_NUMBER",
"value": "2923-18-4"
},
{
"type": "PUBCHEM_CID",
"value": "517019"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCC2=NCCCN2CC1"
},
{
"type": "NAME",
"value": "DBU"
},
{
"type": "NAME",
"value": "1,8-diazabicyclo[5.4.0]undec-7-ene"
},
{
"type": "CAS_NUMBER",
"value": "6674-22-2"
},
{
"type": "PUBCHEM_CID",
"value": "81184"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 2
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"details": "Tri-tert-butylphosphonium tetrafluoroborate: SI Figure 35 (sulfonamide chemical space) draws this ligand as 'PtBu3.HBF4'; the SURF file names it 'P(tBu)3'. The Suzuki campaign (SI Figure 39) used free P(t-Bu)3.",
"value": "CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.F[B-](F)(F)F"
},
{
"type": "NAME",
"value": "PtBu3·HBF4"
},
{
"type": "NAME",
"details": "Name used in the SURF source file",
"value": "P(tBu)3"
},
{
"type": "NAME",
"value": "tri-tert-butylphosphonium tetrafluoroborate (PtBu3·HBF4)"
},
{
"type": "CAS_NUMBER",
"value": "131274-22-1"
},
{
"type": "PUBCHEM_CID",
"value": "2734635"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "CAS_NUMBER",
"value": "75-05-8"
},
{
"type": "PUBCHEM_CID",
"value": "6342"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 6 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[6] | Record 7 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: PtBu3·HBF4 SOLVENT: di-isopropyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[6]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"details": "Tri-tert-butylphosphonium tetrafluoroborate: SI Figure 35 (sulfonamide chemical space) draws this ligand as 'PtBu3.HBF4'; the SURF file names it 'P(tBu)3'. The Suzuki campaign (SI Figure 39) used free P(t-Bu)3.",
"value": "CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.F[B-](F)(F)F"
},
{
"type": "NAME",
"value": "PtBu3·HBF4"
},
{
"type": "NAME",
"details": "Name used in the SURF source file",
"value": "P(tBu)3"
},
{
"type": "NAME",
"value": "tri-tert-butylphosphonium tetrafluoroborate (PtBu3·HBF4)"
},
{
"type": "CAS_NUMBER",
"value": "131274-22-1"
},
{
"type": "PUBCHEM_CID",
"value": "2734635"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)OC(C)C"
},
{
"type": "NAME",
"value": "di-isopropyl ether"
},
{
"type": "NAME",
"value": "diisopropyl ether"
},
{
"type": "CAS_NUMBER",
"value": "108-20-3"
},
{
"type": "PUBCHEM_CID",
"value": "7914"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 7 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[7] | Record 8 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: Na2CO3 REACTANT: benzenesulfonamide CATALYST: PtBu3·HBF4 SOLVENT: di-isopropyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[7]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[Na+].[Na+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "Na2CO3"
},
{
"type": "NAME",
"value": "sodium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "497-19-8"
},
{
"type": "PUBCHEM_CID",
"value": "10340"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"details": "Tri-tert-butylphosphonium tetrafluoroborate: SI Figure 35 (sulfonamide chemical space) draws this ligand as 'PtBu3.HBF4'; the SURF file names it 'P(tBu)3'. The Suzuki campaign (SI Figure 39) used free P(t-Bu)3.",
"value": "CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.F[B-](F)(F)F"
},
{
"type": "NAME",
"value": "PtBu3·HBF4"
},
{
"type": "NAME",
"details": "Name used in the SURF source file",
"value": "P(tBu)3"
},
{
"type": "NAME",
"value": "tri-tert-butylphosphonium tetrafluoroborate (PtBu3·HBF4)"
},
{
"type": "CAS_NUMBER",
"value": "131274-22-1"
},
{
"type": "PUBCHEM_CID",
"value": "2734635"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)OC(C)C"
},
{
"type": "NAME",
"value": "di-isopropyl ether"
},
{
"type": "NAME",
"value": "diisopropyl ether"
},
{
"type": "CAS_NUMBER",
"value": "108-20-3"
},
{
"type": "PUBCHEM_CID",
"value": "7914"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 8 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
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}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[8] | Record 9 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: Na2CO3 REACTANT: benzenesulfonamide CATALYST: PtBu3·HBF4 SOLVENT: di-n-butyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[8]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[Na+].[Na+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "Na2CO3"
},
{
"type": "NAME",
"value": "sodium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "497-19-8"
},
{
"type": "PUBCHEM_CID",
"value": "10340"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"details": "Tri-tert-butylphosphonium tetrafluoroborate: SI Figure 35 (sulfonamide chemical space) draws this ligand as 'PtBu3.HBF4'; the SURF file names it 'P(tBu)3'. The Suzuki campaign (SI Figure 39) used free P(t-Bu)3.",
"value": "CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.F[B-](F)(F)F"
},
{
"type": "NAME",
"value": "PtBu3·HBF4"
},
{
"type": "NAME",
"details": "Name used in the SURF source file",
"value": "P(tBu)3"
},
{
"type": "NAME",
"value": "tri-tert-butylphosphonium tetrafluoroborate (PtBu3·HBF4)"
},
{
"type": "CAS_NUMBER",
"value": "131274-22-1"
},
{
"type": "PUBCHEM_CID",
"value": "2734635"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCCOCCCC"
},
{
"type": "NAME",
"value": "di-n-butyl ether"
},
{
"type": "NAME",
"value": "dibutyl ether"
},
{
"type": "CAS_NUMBER",
"value": "142-96-1"
},
{
"type": "PUBCHEM_CID",
"value": "8909"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 9 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[9] | Record 10 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(OAc)2] REAGENT: DBU REACTANT: benzenesulfonamide CATALYST: PtBu3·HBF4 SOLVENT: cyclopentyl-methyl-ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[9]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(OAc)2]"
},
{
"type": "NAME",
"value": "palladium(II) acetate"
},
{
"type": "CAS_NUMBER",
"value": "3375-31-3"
},
{
"type": "PUBCHEM_CID",
"value": "167845"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCC2=NCCCN2CC1"
},
{
"type": "NAME",
"value": "DBU"
},
{
"type": "NAME",
"value": "1,8-diazabicyclo[5.4.0]undec-7-ene"
},
{
"type": "CAS_NUMBER",
"value": "6674-22-2"
},
{
"type": "PUBCHEM_CID",
"value": "81184"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 2
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"details": "Tri-tert-butylphosphonium tetrafluoroborate: SI Figure 35 (sulfonamide chemical space) draws this ligand as 'PtBu3.HBF4'; the SURF file names it 'P(tBu)3'. The Suzuki campaign (SI Figure 39) used free P(t-Bu)3.",
"value": "CC(C)(C)[PH+](C(C)(C)C)C(C)(C)C.F[B-](F)(F)F"
},
{
"type": "NAME",
"value": "PtBu3·HBF4"
},
{
"type": "NAME",
"details": "Name used in the SURF source file",
"value": "P(tBu)3"
},
{
"type": "NAME",
"value": "tri-tert-butylphosphonium tetrafluoroborate (PtBu3·HBF4)"
},
{
"type": "CAS_NUMBER",
"value": "131274-22-1"
},
{
"type": "PUBCHEM_CID",
"value": "2734635"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1CCCC1"
},
{
"type": "NAME",
"value": "cyclopentyl-methyl-ether"
},
{
"type": "NAME",
"value": "cyclopentyl methyl ether"
},
{
"type": "CAS_NUMBER",
"value": "5614-37-9"
},
{
"type": "PUBCHEM_CID",
"value": "138539"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 10 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
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"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[10] | Record 11 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: JohnPhos SOLVENT: di-isopropyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 13% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 36.6% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[10]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "JohnPhos"
},
{
"type": "NAME",
"value": "2-(Di-tert-butylphosphino)biphenyl"
},
{
"type": "CAS_NUMBER",
"value": "224311-51-7"
},
{
"type": "PUBCHEM_CID",
"value": "2734215"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)OC(C)C"
},
{
"type": "NAME",
"value": "di-isopropyl ether"
},
{
"type": "NAME",
"value": "diisopropyl ether"
},
{
"type": "CAS_NUMBER",
"value": "108-20-3"
},
{
"type": "PUBCHEM_CID",
"value": "7914"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 11 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 13
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 36.599998474121094
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[11] | Record 12 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: JohnPhos SOLVENT: di-n-butyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 22.7% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 63.9% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[11]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
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{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
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"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
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],
"amount": {
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},
"reaction_role": "CATALYST",
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{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
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]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "JohnPhos"
},
{
"type": "NAME",
"value": "2-(Di-tert-butylphosphino)biphenyl"
},
{
"type": "CAS_NUMBER",
"value": "224311-51-7"
},
{
"type": "PUBCHEM_CID",
"value": "2734215"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCCOCCCC"
},
{
"type": "NAME",
"value": "di-n-butyl ether"
},
{
"type": "NAME",
"value": "dibutyl ether"
},
{
"type": "CAS_NUMBER",
"value": "142-96-1"
},
{
"type": "PUBCHEM_CID",
"value": "8909"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 12 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
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},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 22.700000762939453
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 63.900001525878906
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[12] | Record 13 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: JohnPhos SOLVENT: cyclopentyl-methyl-ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 5.9% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 20.4% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[12]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "JohnPhos"
},
{
"type": "NAME",
"value": "2-(Di-tert-butylphosphino)biphenyl"
},
{
"type": "CAS_NUMBER",
"value": "224311-51-7"
},
{
"type": "PUBCHEM_CID",
"value": "2734215"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1CCCC1"
},
{
"type": "NAME",
"value": "cyclopentyl-methyl-ether"
},
{
"type": "NAME",
"value": "cyclopentyl methyl ether"
},
{
"type": "CAS_NUMBER",
"value": "5614-37-9"
},
{
"type": "PUBCHEM_CID",
"value": "138539"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 13 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 5.900000095367432
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 20.399999618530273
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[13] | Record 14 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(OAc)2] REAGENT: KOAC REACTANT: benzenesulfonamide CATALYST: P(oTol)3 SOLVENT: n-propyl acetate | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[13]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(OAc)2]"
},
{
"type": "NAME",
"value": "palladium(II) acetate"
},
{
"type": "CAS_NUMBER",
"value": "3375-31-3"
},
{
"type": "PUBCHEM_CID",
"value": "167845"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].[K+]"
},
{
"type": "NAME",
"value": "KOAC"
},
{
"type": "NAME",
"value": "potassium acetate"
},
{
"type": "CAS_NUMBER",
"value": "127-08-2"
},
{
"type": "PUBCHEM_CID",
"value": "517044"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccccc1P(c1ccccc1C)c1ccccc1C"
},
{
"type": "NAME",
"value": "P(oTol)3"
},
{
"type": "NAME",
"value": "Tri(o-tolyl)phosphine"
},
{
"type": "CAS_NUMBER",
"value": "6163-58-2"
},
{
"type": "PUBCHEM_CID",
"value": "80271"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCOC(C)=O"
},
{
"type": "NAME",
"value": "n-propyl acetate"
},
{
"type": "NAME",
"value": "propyl acetate"
},
{
"type": "CAS_NUMBER",
"value": "109-60-4"
},
{
"type": "PUBCHEM_CID",
"value": "7997"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 14 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[14] | Record 15 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: diisopropylethylamine REACTANT: benzenesulfonamide CATALYST: cataCXium ABn SOLVENT: acetonitrile | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[14]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCN(C(C)C)C(C)C"
},
{
"type": "NAME",
"value": "diisopropylethylamine"
},
{
"type": "NAME",
"value": "N,N-diisopropylethylamine"
},
{
"type": "CAS_NUMBER",
"value": "7087-68-5"
},
{
"type": "PUBCHEM_CID",
"value": "81531"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 2
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)cc1"
},
{
"type": "NAME",
"value": "cataCXium ABn"
},
{
"type": "NAME",
"value": "benzyldi(1-adamantyl)phosphine"
},
{
"type": "CAS_NUMBER",
"value": "395116-70-8"
},
{
"type": "PUBCHEM_CID",
"value": "11271420"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "CAS_NUMBER",
"value": "75-05-8"
},
{
"type": "PUBCHEM_CID",
"value": "6342"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 15 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[15] | Record 16 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium ABn SOLVENT: n-propyl acetate | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[15]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)cc1"
},
{
"type": "NAME",
"value": "cataCXium ABn"
},
{
"type": "NAME",
"value": "benzyldi(1-adamantyl)phosphine"
},
{
"type": "CAS_NUMBER",
"value": "395116-70-8"
},
{
"type": "PUBCHEM_CID",
"value": "11271420"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCOC(C)=O"
},
{
"type": "NAME",
"value": "n-propyl acetate"
},
{
"type": "NAME",
"value": "propyl acetate"
},
{
"type": "CAS_NUMBER",
"value": "109-60-4"
},
{
"type": "PUBCHEM_CID",
"value": "7997"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 16 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[16] | Record 17 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium ABn SOLVENT: di-isopropyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[16]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)cc1"
},
{
"type": "NAME",
"value": "cataCXium ABn"
},
{
"type": "NAME",
"value": "benzyldi(1-adamantyl)phosphine"
},
{
"type": "CAS_NUMBER",
"value": "395116-70-8"
},
{
"type": "PUBCHEM_CID",
"value": "11271420"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)OC(C)C"
},
{
"type": "NAME",
"value": "di-isopropyl ether"
},
{
"type": "NAME",
"value": "diisopropyl ether"
},
{
"type": "CAS_NUMBER",
"value": "108-20-3"
},
{
"type": "PUBCHEM_CID",
"value": "7914"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 17 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
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"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[17] | Record 18 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium ABn SOLVENT: isoamyl acetate | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[17]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
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"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)cc1"
},
{
"type": "NAME",
"value": "cataCXium ABn"
},
{
"type": "NAME",
"value": "benzyldi(1-adamantyl)phosphine"
},
{
"type": "CAS_NUMBER",
"value": "395116-70-8"
},
{
"type": "PUBCHEM_CID",
"value": "11271420"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)CCOC(C)=O"
},
{
"type": "NAME",
"value": "isoamyl acetate"
},
{
"type": "NAME",
"value": "3-methylbutyl acetate"
},
{
"type": "CAS_NUMBER",
"value": "123-92-2"
},
{
"type": "PUBCHEM_CID",
"value": "31276"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 18 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[18] | Record 19 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: KOAC REACTANT: benzenesulfonamide CATALYST: cataCXium ABn SOLVENT: di-n-butyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[18]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
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{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].[K+]"
},
{
"type": "NAME",
"value": "KOAC"
},
{
"type": "NAME",
"value": "potassium acetate"
},
{
"type": "CAS_NUMBER",
"value": "127-08-2"
},
{
"type": "PUBCHEM_CID",
"value": "517044"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)cc1"
},
{
"type": "NAME",
"value": "cataCXium ABn"
},
{
"type": "NAME",
"value": "benzyldi(1-adamantyl)phosphine"
},
{
"type": "CAS_NUMBER",
"value": "395116-70-8"
},
{
"type": "PUBCHEM_CID",
"value": "11271420"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCCOCCCC"
},
{
"type": "NAME",
"value": "di-n-butyl ether"
},
{
"type": "NAME",
"value": "dibutyl ether"
},
{
"type": "CAS_NUMBER",
"value": "142-96-1"
},
{
"type": "PUBCHEM_CID",
"value": "8909"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 19 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[19] | Record 20 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium ABn SOLVENT: di-n-butyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[19]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
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"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
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{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
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],
"amount": {
"moles": {
"value": 2.1029999256134033,
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},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)cc1"
},
{
"type": "NAME",
"value": "cataCXium ABn"
},
{
"type": "NAME",
"value": "benzyldi(1-adamantyl)phosphine"
},
{
"type": "CAS_NUMBER",
"value": "395116-70-8"
},
{
"type": "PUBCHEM_CID",
"value": "11271420"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCCOCCCC"
},
{
"type": "NAME",
"value": "di-n-butyl ether"
},
{
"type": "NAME",
"value": "dibutyl ether"
},
{
"type": "CAS_NUMBER",
"value": "142-96-1"
},
{
"type": "PUBCHEM_CID",
"value": "8909"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 20 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
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}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
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"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
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"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[20] | Record 21 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium ABn SOLVENT: cyclopentyl-methyl-ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[20]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
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{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
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"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)cc1"
},
{
"type": "NAME",
"value": "cataCXium ABn"
},
{
"type": "NAME",
"value": "benzyldi(1-adamantyl)phosphine"
},
{
"type": "CAS_NUMBER",
"value": "395116-70-8"
},
{
"type": "PUBCHEM_CID",
"value": "11271420"
}
],
"amount": {
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"value": 2.1029999256134033,
"units": "MICROMOLE"
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},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1CCCC1"
},
{
"type": "NAME",
"value": "cyclopentyl-methyl-ether"
},
{
"type": "NAME",
"value": "cyclopentyl methyl ether"
},
{
"type": "CAS_NUMBER",
"value": "5614-37-9"
},
{
"type": "PUBCHEM_CID",
"value": "138539"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
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}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
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"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 21 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[21] | Record 22 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium ABn SOLVENT: 2-methyl-2-butanol | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[21]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)cc1"
},
{
"type": "NAME",
"value": "cataCXium ABn"
},
{
"type": "NAME",
"value": "benzyldi(1-adamantyl)phosphine"
},
{
"type": "CAS_NUMBER",
"value": "395116-70-8"
},
{
"type": "PUBCHEM_CID",
"value": "11271420"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "2-methyl-2-butanol"
},
{
"type": "NAME",
"value": "2-methylbutan-2-ol (tert-amyl alcohol)"
},
{
"type": "CAS_NUMBER",
"value": "75-85-4"
},
{
"type": "PUBCHEM_CID",
"value": "6405"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 22 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[22] | Record 23 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium ABn SOLVENT: 2-MeTHF | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[22]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(CP(C23CC4CC(CC(C4)C2)C3)C23CC4CC(CC(C4)C2)C3)cc1"
},
{
"type": "NAME",
"value": "cataCXium ABn"
},
{
"type": "NAME",
"value": "benzyldi(1-adamantyl)phosphine"
},
{
"type": "CAS_NUMBER",
"value": "395116-70-8"
},
{
"type": "PUBCHEM_CID",
"value": "11271420"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC1CCCO1"
},
{
"type": "NAME",
"value": "2-MeTHF"
},
{
"type": "NAME",
"value": "2-methyltetrahydrofuran"
},
{
"type": "CAS_NUMBER",
"value": "96-47-9"
},
{
"type": "PUBCHEM_CID",
"value": "7301"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 23 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[23] | Record 24 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium A SOLVENT: di-isopropyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[23]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2"
},
{
"type": "NAME",
"value": "cataCXium A"
},
{
"type": "NAME",
"value": "di(1-adamantyl)-n-butylphosphine"
},
{
"type": "CAS_NUMBER",
"value": "321921-71-5"
},
{
"type": "PUBCHEM_CID",
"value": "11371790"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)OC(C)C"
},
{
"type": "NAME",
"value": "di-isopropyl ether"
},
{
"type": "NAME",
"value": "diisopropyl ether"
},
{
"type": "CAS_NUMBER",
"value": "108-20-3"
},
{
"type": "PUBCHEM_CID",
"value": "7914"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 24 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[24] | Record 25 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium A SOLVENT: 2-MeTHF | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[24]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCCP(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2"
},
{
"type": "NAME",
"value": "cataCXium A"
},
{
"type": "NAME",
"value": "di(1-adamantyl)-n-butylphosphine"
},
{
"type": "CAS_NUMBER",
"value": "321921-71-5"
},
{
"type": "PUBCHEM_CID",
"value": "11371790"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC1CCCO1"
},
{
"type": "NAME",
"value": "2-MeTHF"
},
{
"type": "NAME",
"value": "2-methyltetrahydrofuran"
},
{
"type": "CAS_NUMBER",
"value": "96-47-9"
},
{
"type": "PUBCHEM_CID",
"value": "7301"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 25 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[25] | Record 26 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: NaTFA REAGENT: DBU REACTANT: benzenesulfonamide CATALYST: cataCXium POMetB SOLVENT: acetonitrile | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[25]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])C(F)(F)F.[Na+]"
},
{
"type": "NAME",
"value": "NaTFA"
},
{
"type": "NAME",
"value": "sodium trifluoroacetate"
},
{
"type": "CAS_NUMBER",
"value": "2923-18-4"
},
{
"type": "PUBCHEM_CID",
"value": "517019"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCC2=NCCCN2CC1"
},
{
"type": "NAME",
"value": "DBU"
},
{
"type": "NAME",
"value": "1,8-diazabicyclo[5.4.0]undec-7-ene"
},
{
"type": "CAS_NUMBER",
"value": "6674-22-2"
},
{
"type": "PUBCHEM_CID",
"value": "81184"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 2
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccccc1-n1cccc1P(C(C)(C)C)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium POMetB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "1053658-91-5"
},
{
"type": "PUBCHEM_CID",
"value": "46919526"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "CAS_NUMBER",
"value": "75-05-8"
},
{
"type": "PUBCHEM_CID",
"value": "6342"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 26 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[26] | Record 27 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium POMetB SOLVENT: di-isopropyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 26% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 56.6% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[26]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccccc1-n1cccc1P(C(C)(C)C)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium POMetB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "1053658-91-5"
},
{
"type": "PUBCHEM_CID",
"value": "46919526"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)OC(C)C"
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{
"type": "NAME",
"value": "di-isopropyl ether"
},
{
"type": "NAME",
"value": "diisopropyl ether"
},
{
"type": "CAS_NUMBER",
"value": "108-20-3"
},
{
"type": "PUBCHEM_CID",
"value": "7914"
}
],
"amount": {
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"units": "MICROLITER"
}
},
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],
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},
"setup": {
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"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
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"is_automated": true,
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"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 27 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 26
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 56.599998474121094
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
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"doi": "10.48550/arXiv.2509.11798",
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"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[27] | Record 28 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium POMetB SOLVENT: isoamyl acetate | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 19.9% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 51.7% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[27]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
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{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
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}
],
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{
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{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
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{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
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{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
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"units": "MICROMOLE"
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},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
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{
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{
"type": "SMILES",
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{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
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],
"amount": {
"moles": {
"value": 2.1029999256134033,
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{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
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]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccccc1-n1cccc1P(C(C)(C)C)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium POMetB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "1053658-91-5"
},
{
"type": "PUBCHEM_CID",
"value": "46919526"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)CCOC(C)=O"
},
{
"type": "NAME",
"value": "isoamyl acetate"
},
{
"type": "NAME",
"value": "3-methylbutyl acetate"
},
{
"type": "CAS_NUMBER",
"value": "123-92-2"
},
{
"type": "PUBCHEM_CID",
"value": "31276"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
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"rpm": 400
}
}
},
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},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
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],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
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{
"identifiers": [
{
"type": "SMILES",
"value": "O"
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{
"type": "NAME",
"value": "water"
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"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
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"type": "AGITATION"
}
},
{
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"volume": {
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}
}
}
],
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{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
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}
},
{
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},
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"type": "CUSTOM",
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],
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],
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}
}
],
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"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[28] | Record 29 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium POMetB SOLVENT: di-n-butyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 25.1% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 72.4% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[28]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
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"type": "REACTION_TYPE",
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"is_mapped": false
}
],
"inputs": {
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{
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"type": "SMILES",
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{
"type": "NAME",
"value": "4-chloroanisole"
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{
"type": "CAS_NUMBER",
"value": "623-12-1"
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{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
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},
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],
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},
"Pd precursor": {
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{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
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{
"type": "CAS_NUMBER",
"value": "12012-95-2"
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{
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},
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}
],
"addition_order": 1
},
"base": {
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"identifiers": [
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"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
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{
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"value": "K2CO3"
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{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
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],
"amount": {
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"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
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],
"amount": {
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"value": 87.625,
"units": "MICROMOLE"
}
},
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}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccccc1-n1cccc1P(C(C)(C)C)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium POMetB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "1053658-91-5"
},
{
"type": "PUBCHEM_CID",
"value": "46919526"
}
],
"amount": {
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"value": 2.1029999256134033,
"units": "MICROMOLE"
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},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCCOCCCC"
},
{
"type": "NAME",
"value": "di-n-butyl ether"
},
{
"type": "NAME",
"value": "dibutyl ether"
},
{
"type": "CAS_NUMBER",
"value": "142-96-1"
},
{
"type": "PUBCHEM_CID",
"value": "8909"
}
],
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"volume": {
"value": 1,
"units": "MILLILITER"
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},
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"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
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"units": "CELSIUS"
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},
"pressure": {
"control": {
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"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
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"rpm": 400
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},
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"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
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{
"type": "NAME",
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"amount": {
"volume": {
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"units": "MICROLITER"
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},
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{
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{
"type": "SMILES",
"value": "O"
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{
"type": "NAME",
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"amount": {
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]
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},
{
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},
{
"type": "ALIQUOT",
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}
}
],
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{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
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{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
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}
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{
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},
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"type": "CUSTOM",
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}
],
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}
],
"analyses": {
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"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[29] | Record 30 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium POMetB SOLVENT: cyclopentyl-methyl-ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 26.2% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 52.5% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[29]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccccc1-n1cccc1P(C(C)(C)C)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium POMetB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "1053658-91-5"
},
{
"type": "PUBCHEM_CID",
"value": "46919526"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1CCCC1"
},
{
"type": "NAME",
"value": "cyclopentyl-methyl-ether"
},
{
"type": "NAME",
"value": "cyclopentyl methyl ether"
},
{
"type": "CAS_NUMBER",
"value": "5614-37-9"
},
{
"type": "PUBCHEM_CID",
"value": "138539"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 30 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 26.200000762939453
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 52.5
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[30] | Record 31 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium POMetB SOLVENT: 2-MeTHF | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 37% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 72.6% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[30]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
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"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccccc1-n1cccc1P(C(C)(C)C)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium POMetB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "1053658-91-5"
},
{
"type": "PUBCHEM_CID",
"value": "46919526"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC1CCCO1"
},
{
"type": "NAME",
"value": "2-MeTHF"
},
{
"type": "NAME",
"value": "2-methyltetrahydrofuran"
},
{
"type": "CAS_NUMBER",
"value": "96-47-9"
},
{
"type": "PUBCHEM_CID",
"value": "7301"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 31 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 37
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 72.5999984741211
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[31] | Record 32 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(OAc)2] REAGENT: DBU REACTANT: benzenesulfonamide CATALYST: cataCXium POMeCy SOLVENT: 2-methyl-2-butanol | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[31]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(OAc)2]"
},
{
"type": "NAME",
"value": "palladium(II) acetate"
},
{
"type": "CAS_NUMBER",
"value": "3375-31-3"
},
{
"type": "PUBCHEM_CID",
"value": "167845"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCC2=NCCCN2CC1"
},
{
"type": "NAME",
"value": "DBU"
},
{
"type": "NAME",
"value": "1,8-diazabicyclo[5.4.0]undec-7-ene"
},
{
"type": "CAS_NUMBER",
"value": "6674-22-2"
},
{
"type": "PUBCHEM_CID",
"value": "81184"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 2
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccccc1-n1cccc1P(C1CCCCC1)C1CCCCC1"
},
{
"type": "NAME",
"value": "cataCXium POMeCy"
},
{
"type": "NAME",
"value": "2-(dicyclohexylphosphino)-1-(2-methoxyphenyl)-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "672937-63-2"
},
{
"type": "PUBCHEM_CID",
"value": "53411820"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "2-methyl-2-butanol"
},
{
"type": "NAME",
"value": "2-methylbutan-2-ol (tert-amyl alcohol)"
},
{
"type": "CAS_NUMBER",
"value": "75-85-4"
},
{
"type": "PUBCHEM_CID",
"value": "6405"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 32 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
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"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[32] | Record 33 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: acetonitrile | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[32]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
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"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
},
{
"type": "CAS_NUMBER",
"value": "75-05-8"
},
{
"type": "PUBCHEM_CID",
"value": "6342"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 33 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[33] | Record 34 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: anisole | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 14% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 32.6% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[33]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
},
{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccccc1"
},
{
"type": "NAME",
"value": "anisole"
},
{
"type": "CAS_NUMBER",
"value": "100-66-3"
},
{
"type": "PUBCHEM_CID",
"value": "7519"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 34 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
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"stirring": {
"type": "AGITATION"
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},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 14
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 32.599998474121094
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
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}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
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"time": {
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},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[34] | Record 35 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: mesitylene | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 11.8% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 27.9% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[34]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
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{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
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],
"inputs": {
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{
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{
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{
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{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
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{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
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"units": "MICROMOLE"
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},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
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"Pd precursor": {
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{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
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"amount": {
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{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
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]
}
],
"addition_order": 1
},
"base": {
"components": [
{
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{
"type": "SMILES",
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{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
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],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
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"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1cc(C)cc(C)c1"
},
{
"type": "NAME",
"value": "mesitylene"
},
{
"type": "NAME",
"value": "1,3,5-trimethylbenzene"
},
{
"type": "CAS_NUMBER",
"value": "108-67-8"
},
{
"type": "PUBCHEM_CID",
"value": "7947"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 35 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
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],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
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}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 27.899999618530273
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
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"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[35] | Record 36 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: n-propyl acetate | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 5.7% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 16.1% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[35]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
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{
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{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
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"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
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},
"reaction_role": "CATALYST",
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],
"addition_order": 1
},
"base": {
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{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
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{
"type": "NAME",
"value": "K2CO3"
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{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
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{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
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"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCOC(C)=O"
},
{
"type": "NAME",
"value": "n-propyl acetate"
},
{
"type": "NAME",
"value": "propyl acetate"
},
{
"type": "CAS_NUMBER",
"value": "109-60-4"
},
{
"type": "PUBCHEM_CID",
"value": "7997"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 36 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
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{
"type": "NAME",
"value": "water"
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],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
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"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 5.699999809265137
}
},
{
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"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 16.100000381469727
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
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}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
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},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[36] | Record 37 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd2(dba)3] REAGENT: NaTFA REAGENT: DBU REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: n-propyl acetate | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[36]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
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},
{
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{
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{
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{
"type": "NAME",
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{
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{
"identifiers": [
{
"type": "SMILES",
"details": "Labelled '[Pd(dba)3]' in SI Figures 36 and 40; recorded as Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(0)), following the SURF files and main-text Figure 6a.",
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},
{
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"value": "[Pd2(dba)3]"
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{
"type": "NAME",
"value": "tris(dibenzylideneacetone)dipalladium(0)"
},
{
"type": "CAS_NUMBER",
"value": "51364-51-3"
},
{
"type": "PUBCHEM_CID",
"value": "9811564"
}
],
"amount": {
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"reaction_role": "CATALYST",
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"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base 1": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C([O-])C(F)(F)F.[Na+]"
},
{
"type": "NAME",
"value": "NaTFA"
},
{
"type": "NAME",
"value": "sodium trifluoroacetate"
},
{
"type": "CAS_NUMBER",
"value": "2923-18-4"
},
{
"type": "PUBCHEM_CID",
"value": "517019"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"base 2": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCC2=NCCCN2CC1"
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{
"type": "NAME",
"value": "DBU"
},
{
"type": "NAME",
"value": "1,8-diazabicyclo[5.4.0]undec-7-ene"
},
{
"type": "CAS_NUMBER",
"value": "6674-22-2"
},
{
"type": "PUBCHEM_CID",
"value": "81184"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 2
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCOC(C)=O"
},
{
"type": "NAME",
"value": "n-propyl acetate"
},
{
"type": "NAME",
"value": "propyl acetate"
},
{
"type": "CAS_NUMBER",
"value": "109-60-4"
},
{
"type": "PUBCHEM_CID",
"value": "7997"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 37 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[37] | Record 38 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: di-isopropyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 11% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 28% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[37]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
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{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
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],
"amount": {
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"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
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},
"reaction_role": "CATALYST",
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"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
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{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
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"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
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{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
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"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)OC(C)C"
},
{
"type": "NAME",
"value": "di-isopropyl ether"
},
{
"type": "NAME",
"value": "diisopropyl ether"
},
{
"type": "CAS_NUMBER",
"value": "108-20-3"
},
{
"type": "PUBCHEM_CID",
"value": "7914"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 38 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
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"units": "MINUTE"
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{
"type": "ALIQUOT",
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"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 11
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
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"percentage": {
"value": 28
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
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}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
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},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[38] | Record 39 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: isoamyl acetate | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 5.7% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 14.9% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[38]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
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{
"type": "NAME",
"value": "4-chloroanisole"
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{
"type": "CAS_NUMBER",
"value": "623-12-1"
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{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
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{
"type": "SMILES",
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{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
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"type": "CAS_NUMBER",
"value": "12012-95-2"
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{
"type": "PUBCHEM_CID",
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],
"addition_order": 1
},
"base": {
"components": [
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"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
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{
"type": "NAME",
"value": "K2CO3"
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{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
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{
"type": "NAME",
"value": "benzenesulfonamide"
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{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
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],
"amount": {
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"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)CCOC(C)=O"
},
{
"type": "NAME",
"value": "isoamyl acetate"
},
{
"type": "NAME",
"value": "3-methylbutyl acetate"
},
{
"type": "CAS_NUMBER",
"value": "123-92-2"
},
{
"type": "PUBCHEM_CID",
"value": "31276"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
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"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
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},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 39 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
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"temperature": {
"control": {
"type": "AMBIENT"
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}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
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{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
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"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
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{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
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}
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{
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"percentage": {
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},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
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"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
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}
}
],
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"doi": "10.48550/arXiv.2509.11798",
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"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[39] | Record 40 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: di-n-butyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 5% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[39]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
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{
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{
"type": "SMILES",
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{
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{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
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],
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"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
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],
"amount": {
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"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
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"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
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],
"addition_order": 1
},
"base": {
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{
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{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
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{
"type": "NAME",
"value": "K2CO3"
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{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
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{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
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],
"amount": {
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"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
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],
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"units": "MICROMOLE"
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]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCCOCCCC"
},
{
"type": "NAME",
"value": "di-n-butyl ether"
},
{
"type": "NAME",
"value": "dibutyl ether"
},
{
"type": "CAS_NUMBER",
"value": "142-96-1"
},
{
"type": "PUBCHEM_CID",
"value": "8909"
}
],
"amount": {
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"units": "MICROLITER"
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},
"reaction_role": "SOLVENT"
}
],
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}
},
"setup": {
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"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 40 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
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"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 5
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
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}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
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"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[40] | Record 41 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: cyclopentyl-methyl-ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 11.5% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 32.5% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[40]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
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"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
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],
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{
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{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
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{
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"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
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{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
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},
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}
],
"addition_order": 2
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{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
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{
"type": "CUSTOM",
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}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1CCCC1"
},
{
"type": "NAME",
"value": "cyclopentyl-methyl-ether"
},
{
"type": "NAME",
"value": "cyclopentyl methyl ether"
},
{
"type": "CAS_NUMBER",
"value": "5614-37-9"
},
{
"type": "PUBCHEM_CID",
"value": "138539"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
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},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 41 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
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],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 11.5
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 32.5
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
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"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[41] | Record 42 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(OAc)2] REAGENT: DBU REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: cyclopentyl-methyl-ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[41]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
"1-chloro-4-methoxy-benzene": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
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{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
"moles": {
"value": 70.0999984741211,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(=O)[O-].CC(=O)[O-].[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(OAc)2]"
},
{
"type": "NAME",
"value": "palladium(II) acetate"
},
{
"type": "CAS_NUMBER",
"value": "3375-31-3"
},
{
"type": "PUBCHEM_CID",
"value": "167845"
}
],
"amount": {
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"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST",
"preparations": [
{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "C1CCC2=NCCCN2CC1"
},
{
"type": "NAME",
"value": "DBU"
},
{
"type": "NAME",
"value": "1,8-diazabicyclo[5.4.0]undec-7-ene"
},
{
"type": "CAS_NUMBER",
"value": "6674-22-2"
},
{
"type": "PUBCHEM_CID",
"value": "81184"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 2
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
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],
"amount": {
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"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
}
],
"amount": {
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"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
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]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1CCCC1"
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{
"type": "NAME",
"value": "cyclopentyl-methyl-ether"
},
{
"type": "NAME",
"value": "cyclopentyl methyl ether"
},
{
"type": "CAS_NUMBER",
"value": "5614-37-9"
},
{
"type": "PUBCHEM_CID",
"value": "138539"
}
],
"amount": {
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"units": "MICROLITER"
}
},
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}
],
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}
},
"setup": {
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"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
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"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 42 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 0
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 0
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[42] | Record 43 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: 2-methyl-2-butanol | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 12.2% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 28.2% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[42]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
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],
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{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
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{
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"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
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{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
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],
"amount": {
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},
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}
],
"addition_order": 2
},
"Pd precursor": {
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{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
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{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
}
]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
},
{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCC(C)(C)O"
},
{
"type": "NAME",
"value": "2-methyl-2-butanol"
},
{
"type": "NAME",
"value": "2-methylbutan-2-ol (tert-amyl alcohol)"
},
{
"type": "CAS_NUMBER",
"value": "75-85-4"
},
{
"type": "PUBCHEM_CID",
"value": "6405"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 43 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
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{
"type": "NAME",
"value": "water"
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"amount": {
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"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
"stirring": {
"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
"details": "50 µL sample taken for LC-MS analysis",
"amount": {
"volume": {
"value": 50,
"units": "MICROLITER"
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}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 12.199999809265137
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 28.200000762939453
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
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"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
"provenance": {
"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[43] | Record 44 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PIntB SOLVENT: 2-MeTHF | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 8% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 27.1% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[43]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
},
{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
"is_mapped": false
}
],
"inputs": {
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"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(Cl)cc1"
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{
"type": "NAME",
"value": "1-chloro-4-methoxy-benzene"
},
{
"type": "NAME",
"value": "4-chloroanisole"
},
{
"type": "CAS_NUMBER",
"value": "623-12-1"
},
{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
"amount": {
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"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
}
],
"addition_order": 2
},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
},
{
"type": "PUBCHEM_CID",
"value": "61538"
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],
"amount": {
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],
"addition_order": 1
},
"base": {
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{
"identifiers": [
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"type": "SMILES",
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"type": "NAME",
"value": "K2CO3"
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{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
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{
"type": "PUBCHEM_CID",
"value": "11430"
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],
"amount": {
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"value": 175.25,
"units": "MICROMOLE"
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},
"reaction_role": "REAGENT"
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],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
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{
"type": "NAME",
"value": "benzenesulfonamide"
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{
"type": "CAS_NUMBER",
"value": "98-10-2"
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{
"type": "PUBCHEM_CID",
"value": "7370"
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],
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"value": 87.625,
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},
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],
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},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cc2ccccc2n1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PIntB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-indole"
},
{
"type": "CAS_NUMBER",
"value": "740815-37-6"
},
{
"type": "PUBCHEM_CID",
"value": "11175133"
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],
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]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC1CCCO1"
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{
"type": "NAME",
"value": "2-MeTHF"
},
{
"type": "NAME",
"value": "2-methyltetrahydrofuran"
},
{
"type": "CAS_NUMBER",
"value": "96-47-9"
},
{
"type": "PUBCHEM_CID",
"value": "7301"
}
],
"amount": {
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],
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},
"setup": {
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"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
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"units": "MILLILITER"
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"is_automated": true,
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"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
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},
"pressure": {
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"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 44 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
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"temperature": {
"control": {
"type": "AMBIENT"
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},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
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],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
},
{
"identifiers": [
{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
}
],
"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
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"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
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"value": 20,
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"type": "AGITATION"
}
},
{
"type": "ALIQUOT",
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"volume": {
"value": 50,
"units": "MICROLITER"
}
}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 8
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 27.100000381469727
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
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}
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],
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"doi": "10.48550/arXiv.2509.11798",
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"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[44] | Record 45 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PtB SOLVENT: mesitylene | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 30.8% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 56% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[44]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
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"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
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{
"type": "NAME",
"value": "4-chloroanisole"
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"type": "PUBCHEM_CID",
"value": "12167"
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],
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{
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{
"type": "NAME",
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{
"type": "CAS_NUMBER",
"value": "12012-95-2"
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"type": "PUBCHEM_CID",
"value": "61538"
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"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
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{
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{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
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{
"type": "NAME",
"value": "K2CO3"
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{
"type": "NAME",
"value": "potassium carbonate"
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{
"type": "CAS_NUMBER",
"value": "584-08-7"
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{
"type": "PUBCHEM_CID",
"value": "11430"
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],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
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{
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{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
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{
"type": "NAME",
"value": "benzenesulfonamide"
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{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cccn1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PtB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "672937-61-0"
},
{
"type": "PUBCHEM_CID",
"value": "11403475"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1cc(C)cc(C)c1"
},
{
"type": "NAME",
"value": "mesitylene"
},
{
"type": "NAME",
"value": "1,3,5-trimethylbenzene"
},
{
"type": "CAS_NUMBER",
"value": "108-67-8"
},
{
"type": "PUBCHEM_CID",
"value": "7947"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
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"setup": {
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"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
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"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
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},
"pressure": {
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"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
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"rpm": 400
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}
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"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
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{
"type": "NAME",
"value": "acetonitrile"
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"amount": {
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"units": "MICROLITER"
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"units": "MICROLITER"
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},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
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},
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],
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{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
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{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
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{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
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{
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"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
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],
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},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[45] | Record 46 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PtB SOLVENT: di-isopropyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 13.6% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 37.2% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[45]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
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"is_mapped": false
}
],
"inputs": {
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{
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{
"type": "NAME",
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{
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"value": "12167"
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}
},
"reaction_role": "REACTANT",
"is_limiting": true
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],
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"Pd precursor": {
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{
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{
"type": "SMILES",
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},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
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{
"type": "CAS_NUMBER",
"value": "12012-95-2"
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"reaction_role": "CATALYST",
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],
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"base": {
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{
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{
"type": "CAS_NUMBER",
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"amount": {
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},
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],
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},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
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"type": "NAME",
"value": "benzenesulfonamide"
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{
"type": "CAS_NUMBER",
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"type": "PUBCHEM_CID",
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],
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},
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],
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},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cccn1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PtB"
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{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-pyrrole"
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{
"type": "CAS_NUMBER",
"value": "672937-61-0"
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"type": "PUBCHEM_CID",
"value": "11403475"
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"solvent": {
"components": [
{
"identifiers": [
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"type": "SMILES",
"value": "CC(C)OC(C)C"
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{
"type": "NAME",
"value": "di-isopropyl ether"
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{
"type": "NAME",
"value": "diisopropyl ether"
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{
"type": "CAS_NUMBER",
"value": "108-20-3"
},
{
"type": "PUBCHEM_CID",
"value": "7914"
}
],
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"units": "MILLILITER"
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},
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},
"setpoint": {
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"units": "CELSIUS"
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"pressure": {
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},
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"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
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"rpm": 400
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"workups": [
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"type": "ADDITION",
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"type": "SMILES",
"value": "CC#N"
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{
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"amount": {
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"units": "MICROLITER"
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},
"reaction_role": "WORKUP"
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{
"identifiers": [
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"type": "SMILES",
"value": "O"
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{
"type": "NAME",
"value": "water"
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],
"amount": {
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"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
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"duration": {
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},
{
"type": "ALIQUOT",
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}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
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"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
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],
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"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
"uses_internal_standard": false,
"percentage": {
"value": 13.600000381469727
}
},
{
"analysis_key": "LCMS",
"type": "SELECTIVITY",
"uses_internal_standard": false,
"percentage": {
"value": 37.20000076293945
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"LCMS": {
"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
"instrument_manufacturer": "Waters"
}
}
}
],
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"doi": "10.48550/arXiv.2509.11798",
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"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[46] | Record 47 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PtB SOLVENT: isoamyl acetate | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 6.6% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 25.5% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[46]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
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{
"type": "REACTION_SMILES",
"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
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],
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{
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{
"type": "NAME",
"value": "4-chloroanisole"
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{
"type": "CAS_NUMBER",
"value": "623-12-1"
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{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
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"value": 70.0999984741211,
"units": "MICROMOLE"
}
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"is_limiting": true
}
],
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{
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{
"type": "SMILES",
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{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
},
{
"type": "CAS_NUMBER",
"value": "12012-95-2"
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{
"type": "PUBCHEM_CID",
"value": "61538"
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{
"type": "CUSTOM",
"details": "Dispensed on ChemBeads (SI sections 7.2 and 8.2)"
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]
}
],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[K+].[K+].[O-]C([O-])=O"
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{
"type": "NAME",
"value": "K2CO3"
},
{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
}
],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
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{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cccn1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PtB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "672937-61-0"
},
{
"type": "PUBCHEM_CID",
"value": "11403475"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)CCOC(C)=O"
},
{
"type": "NAME",
"value": "isoamyl acetate"
},
{
"type": "NAME",
"value": "3-methylbutyl acetate"
},
{
"type": "CAS_NUMBER",
"value": "123-92-2"
},
{
"type": "PUBCHEM_CID",
"value": "31276"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
}
},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": true,
"automation_platform": "Unchained Labs custom HTE platform (two Big Kahuna units, LiCONiC LiCotel store); solids dosed automatically with a Mettler balance, liquids added manually with an Eppendorf Multipette E3",
"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
}
},
"pressure": {
"control": {
"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 47 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
},
"workups": [
{
"type": "TEMPERATURE",
"details": "Plate cooled to room temperature",
"temperature": {
"control": {
"type": "AMBIENT"
}
}
},
{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"volume": {
"value": 400,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
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{
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{
"type": "SMILES",
"value": "O"
},
{
"type": "NAME",
"value": "water"
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"amount": {
"volume": {
"value": 100,
"units": "MICROLITER"
}
},
"reaction_role": "WORKUP"
}
]
}
},
{
"type": "STIRRING",
"details": "Shaken for 20 min at room temperature",
"duration": {
"value": 20,
"units": "MINUTE"
},
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"type": "AGITATION"
}
},
{
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"details": "50 µL sample taken for LC-MS analysis",
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"volume": {
"value": 50,
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}
}
],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
},
{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
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"percentage": {
"value": 6.599999904632568
}
},
{
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"percentage": {
"value": 25.5
},
"selectivity": {
"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
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],
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"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
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}
}
],
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"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||
| reactions[47] | Record 48 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PtB SOLVENT: di-n-butyl ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 15.9% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 47.4% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[47]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
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"is_mapped": false
}
],
"inputs": {
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{
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"type": "SMILES",
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{
"type": "NAME",
"value": "4-chloroanisole"
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{
"type": "CAS_NUMBER",
"value": "623-12-1"
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{
"type": "PUBCHEM_CID",
"value": "12167"
}
],
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"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT",
"is_limiting": true
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],
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},
"Pd precursor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]"
},
{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
},
{
"type": "NAME",
"value": "allylpalladium(II) chloride dimer"
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{
"type": "CAS_NUMBER",
"value": "12012-95-2"
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{
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"reaction_role": "CATALYST",
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],
"addition_order": 1
},
"base": {
"components": [
{
"identifiers": [
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"type": "SMILES",
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{
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{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
},
{
"type": "PUBCHEM_CID",
"value": "11430"
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],
"amount": {
"moles": {
"value": 175.25,
"units": "MICROMOLE"
}
},
"reaction_role": "REAGENT"
}
],
"addition_order": 1
},
"benzenesulfonamide": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
},
{
"type": "NAME",
"value": "benzenesulfonamide"
},
{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
}
],
"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
}
},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cccn1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PtB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "672937-61-0"
},
{
"type": "PUBCHEM_CID",
"value": "11403475"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CCCCOCCCC"
},
{
"type": "NAME",
"value": "di-n-butyl ether"
},
{
"type": "NAME",
"value": "dibutyl ether"
},
{
"type": "CAS_NUMBER",
"value": "142-96-1"
},
{
"type": "PUBCHEM_CID",
"value": "8909"
}
],
"amount": {
"volume": {
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"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
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"units": "MILLILITER"
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"environment": {
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}
},
"conditions": {
"temperature": {
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"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
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"pressure": {
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"type": "SEALED",
"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 48 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets)."
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"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
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{
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{
"type": "SMILES",
"value": "CC#N"
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{
"type": "NAME",
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"amount": {
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"units": "MICROLITER"
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},
"reaction_role": "WORKUP"
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{
"identifiers": [
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"type": "SMILES",
"value": "O"
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{
"type": "NAME",
"value": "water"
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"amount": {
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"units": "MICROLITER"
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"reaction_role": "WORKUP"
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]
}
},
{
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{
"type": "ALIQUOT",
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],
"outcomes": [
{
"reaction_time": {
"value": 18,
"units": "HOUR"
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"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
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"value": "N-(4-methoxyphenyl)benzenesulfonamide"
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],
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"measurements": [
{
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"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
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{
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"type": "CUSTOM",
"details": "LC area-percent (AP) selectivity for the desired product as reported by the authors ('AP selectivity' column of the SURF file, fraction converted to percent). The paper reports it alongside AP yield from the same LCAP analysis but does not give its formula. The paper treats AP yield above AP selectivity as physically impossible (SI section 3.1), yet the source files report AP selectivity 0 for every reaction with AP yield between 0.5% and 5% (105 reactions); these look like a cut-off, not measured values, and are recorded as reported."
}
}
],
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}
],
"analyses": {
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"type": "LCMS",
"details": "Waters ACQUITY UPLC I-Class with QDa mass detector; 50 µL aliquot of the diluted reaction mixture. Peaks were tagged in the HTE OS / Spotfire workflow (Wuitschik et al.); peaks of ligands and precatalyst components were tagged 'ignore peak' and, with solvent peaks, excluded from the LC area-percent (LCAP) calculation (SI section 6).",
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}
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}
} | |||||
| reactions[48] | Record 49 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(allyl)Cl]2 REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PtB SOLVENT: cyclopentyl-methyl-ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 24.7% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 48.8% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[48]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
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{
"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
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"value": "COc1ccc(Cl)cc1.NS(=O)(=O)c1ccccc1>>COc1ccc(NS(=O)(=O)c2ccccc2)cc1",
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{
"type": "NAME",
"value": "4-chloroanisole"
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{
"type": "CAS_NUMBER",
"value": "623-12-1"
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{
"type": "PUBCHEM_CID",
"value": "12167"
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],
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{
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{
"type": "SMILES",
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{
"type": "NAME",
"value": "[Pd(allyl)Cl]2"
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{
"type": "NAME",
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{
"type": "CAS_NUMBER",
"value": "12012-95-2"
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"value": "61538"
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"type": "SMILES",
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{
"type": "NAME",
"value": "K2CO3"
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{
"type": "NAME",
"value": "potassium carbonate"
},
{
"type": "CAS_NUMBER",
"value": "584-08-7"
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{
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"value": "11430"
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"amount": {
"moles": {
"value": 175.25,
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},
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],
"addition_order": 1
},
"benzenesulfonamide": {
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{
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{
"type": "SMILES",
"value": "NS(=O)(=O)c1ccccc1"
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{
"type": "NAME",
"value": "benzenesulfonamide"
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{
"type": "CAS_NUMBER",
"value": "98-10-2"
},
{
"type": "PUBCHEM_CID",
"value": "7370"
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"amount": {
"moles": {
"value": 87.625,
"units": "MICROMOLE"
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},
"reaction_role": "REACTANT"
}
],
"addition_order": 1
},
"ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC(C)(C)P(c1cccn1-c1ccccc1)C(C)(C)C"
},
{
"type": "NAME",
"value": "cataCXium PtB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "672937-61-0"
},
{
"type": "PUBCHEM_CID",
"value": "11403475"
}
],
"amount": {
"moles": {
"value": 2.1029999256134033,
"units": "MICROMOLE"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "COC1CCCC1"
},
{
"type": "NAME",
"value": "cyclopentyl-methyl-ether"
},
{
"type": "NAME",
"value": "cyclopentyl methyl ether"
},
{
"type": "CAS_NUMBER",
"value": "5614-37-9"
},
{
"type": "PUBCHEM_CID",
"value": "138539"
}
],
"amount": {
"volume": {
"value": 150,
"units": "MICROLITER"
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},
"reaction_role": "SOLVENT"
}
],
"addition_order": 2
}
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"setup": {
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"type": "VIAL",
"details": "1 mL vial with a V&P Scientific super tumble stir disc (VP 721F-1) in a standard 96-position parallel synthesis reaction block (Analytical Sales and Services, SKU 96960)",
"volume": {
"value": 1,
"units": "MILLILITER"
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},
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"environment": {
"type": "GLOVE_BOX",
"details": "Platform enclosed in an LC Technology Solutions glove box (SI section 6); the glove box gas is not stated"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "96-position parallel synthesis reaction block on the Big Kahuna reaction-execution unit"
},
"setpoint": {
"value": 70,
"units": "CELSIUS"
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"pressure": {
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"details": "Plate sealed before heating (SI sections 7.2 and 8.2)"
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},
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"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
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{
"type": "ADDITION",
"details": "4/1 MeCN/H2O (500 µL) added to each well",
"input": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
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{
"type": "NAME",
"value": "acetonitrile"
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"amount": {
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"value": 400,
"units": "MICROLITER"
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"type": "SMILES",
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"value": "water"
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]
}
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{
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{
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{
"type": "SMILES",
"value": "COc1ccc(NS(=O)(=O)c2ccccc2)cc1"
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{
"type": "NAME",
"value": "N-(4-methoxyphenyl)benzenesulfonamide"
}
],
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"measurements": [
{
"analysis_key": "LCMS",
"type": "AREA",
"details": "LC area percent (AP) yield of the product as reported by the authors ('AP yield' column of the SURF file, stored there as a fraction and converted to percent here): product peak area as a percentage of the total integrated peak area, excluding solvent peaks and peaks tagged 'ignore peak' (ligand and precatalyst components). Uncalibrated; not a quantitative yield.",
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}
},
{
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},
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"person": {
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"email": "hello@tokensforprogress.org"
}
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} | |||||
| reactions[49] | Record 50 | REACTANT: 1-chloro-4-methoxy-benzene CATALYST: [Pd(OAc)2] REAGENT: K2CO3 REACTANT: benzenesulfonamide CATALYST: cataCXium PtB SOLVENT: cyclopentyl-methyl-ether | 70 CELSIUS | N-(4-methoxyphenyl)benzenesulfonamide · AREA: 0% [LCMS] N-(4-methoxyphenyl)benzenesulfonamide · SELECTIVITY: 0% [LCMS] | 10.48550/arXiv.2509.11798 |
Decoded fields · reactions[49]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
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"type": "REACTION_TYPE",
"value": "Pd-catalysed sulfonamide N-arylation (Buchwald-Hartwig-type C-N coupling)"
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{
"type": "NAME",
"value": "4-chloroanisole"
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{
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"value": "623-12-1"
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{
"type": "PUBCHEM_CID",
"value": "12167"
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{
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{
"type": "SMILES",
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{
"type": "NAME",
"value": "[Pd(OAc)2]"
},
{
"type": "NAME",
"value": "palladium(II) acetate"
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"value": "3375-31-3"
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"value": "167845"
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{
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"value": "potassium carbonate"
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{
"type": "CAS_NUMBER",
"value": "584-08-7"
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{
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"value": "11430"
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],
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},
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"components": [
{
"identifiers": [
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"type": "SMILES",
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"type": "NAME",
"value": "benzenesulfonamide"
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{
"type": "CAS_NUMBER",
"value": "98-10-2"
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],
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],
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"ligand": {
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{
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"type": "SMILES",
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{
"type": "NAME",
"value": "cataCXium PtB"
},
{
"type": "NAME",
"value": "2-(di-tert-butylphosphino)-1-phenyl-1H-pyrrole"
},
{
"type": "CAS_NUMBER",
"value": "672937-61-0"
},
{
"type": "PUBCHEM_CID",
"value": "11403475"
}
],
"amount": {
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{
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"type": "SMILES",
"value": "COC1CCCC1"
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{
"type": "NAME",
"value": "cyclopentyl-methyl-ether"
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{
"type": "NAME",
"value": "cyclopentyl methyl ether"
},
{
"type": "CAS_NUMBER",
"value": "5614-37-9"
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{
"type": "PUBCHEM_CID",
"value": "138539"
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],
"amount": {
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"setpoint": {
"value": 70,
"units": "CELSIUS"
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}
},
"stirring": {
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"details": "Tumble stirring with V&P Scientific super tumble stir discs (VP 721F-1)",
"rate": {
"details": "SURF stirring_shaking value 'st_400'",
"rpm": 400
}
}
},
"notes": {
"procedure_details": "HTE procedure (SI section 7.2): Substrates, solid ligands, palladium precursors (on ChemBeads) and solid bases were dispensed into 1 mL vials with stirring disks in a 96-well plate. 1-chloro-4-methoxy-benzene, liquid ligands, solvents, and liquid bases were added. The plate was sealed and stirred at 70 °C for 18 h, then cooled to rt. 4/1 MeCN/H2O (500 µL) was added to each well and shaken for 20 min at rt. 50 µL samples were taken and analysed by LC-MS. Source: row 50 (1-based, excluding the header) of pd_sulfonamide_SURF.csv (https://github.com/schwallergroup/alphaswarm/tree/641b25882e707b9e0c0a5550703879a39dd3afe8/data/HTE_datasets). Matches one of the 96 conditions of the Sobol sample the paper used for its landscape analysis, identified by the curator by re-running the authors' Sobol initialisation (seed 9)."
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"input": {
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{
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"amount": {
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"reaction_role": "WORKUP"
},
{
"identifiers": [
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},
{
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"value": "N-(4-methoxyphenyl)benzenesulfonamide"
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],
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"uses_internal_standard": false,
"percentage": {
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{
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"percentage": {
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],
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}
],
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}
}
}
],
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"doi": "10.48550/arXiv.2509.11798",
"publication_url": "https://arxiv.org/abs/2509.11798",
"record_created": {
"time": {
"value": "2026-09-26T00:50:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
}
},
"is_mined": false
}
} | |||||