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Table numbers are rounded to 7 significant digits; decoded details retain full precision.
Deolka et al. 2025 JACS: heteroleptic Pd-catalyzed fluorination of arylboronic acids (HTE, EDBO+ optimization, controls, substrate scope)
Dataset description
Reactions from Deolka, Dalmau, Garcia Roca, Vasylevskyi, Samha, Sigman, 'Development of a Heteroleptic Palladium Catalyst for the Fluorination of Arylboronic Acids using Data Science Tools', J. Am. Chem. Soc. 2025, DOI 10.1021/jacs.5c11929, curated from the Supporting Information only. Four parts kept together: (1) 72 HTE wells (Pd-terpyridine complexes C1-C4 x bidentate ligands L1-L6 x 3 arylboronic acids; SI Figs S4-S6 / Substrates.csv; amounts not reported in the SI); (2) 75 EDBO+ Bayesian-optimization experiments (25 condition sets x 3 substrates; 19F NMR yields); (3) 2 control experiments; (4) 32 substrate-scope reactions with C3/L3 (or C12/L13) catalysts and 19F NMR yields. Each catalyst is entered as two separate inputs: the Pd-terpyridine complex and the second bidentate ligand. Isolated yields appear only in the main article and are not included. See per-reaction notes for source discrepancies.
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 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2,2'-bipyridine SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 9% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[0]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L1C1S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccn2)nc1"
},
{
"type": "NAME",
"value": "2,2'-bipyridine"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L1); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 9
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L1C1S1 (Figure S4)."
}
}
} | |||||
| reactions[1] | Record 2 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 47% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[1]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L2C1S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cnc2c(c1)ccc1cccnc12"
},
{
"type": "NAME",
"value": "1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L2); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 47
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L2C1S1 (Figure S4)."
}
}
} | |||||
| reactions[2] | Record 3 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2-methyl-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 60% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[2]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L3C1S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-methyl-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L3); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 60
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L3C1S1 (Figure S4)."
}
}
} | |||||
| reactions[3] | Record 4 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2-chloro-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 45% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[3]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L4C1S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-chloro-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L4); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 45
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L4C1S1 (Figure S4)."
}
}
} | |||||
| reactions[4] | Record 5 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 4,5-diazafluoren-9-one SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 8% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[4]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L5C1S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "4,5-diazafluoren-9-one"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L5); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 8
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L5C1S1 (Figure S4)."
}
}
} | |||||
| reactions[5] | Record 6 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 6% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[5]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L6C1S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2c(c1)-c1ccccc1C21c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene]"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L6); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 6
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L6C1S1 (Figure S4)."
}
}
} | |||||
| reactions[6] | Record 7 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2,2'-bipyridine SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 19% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[6]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L1C2S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccn2)nc1"
},
{
"type": "NAME",
"value": "2,2'-bipyridine"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L1); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 19
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L1C2S1 (Figure S4)."
}
}
} | |||||
| reactions[7] | Record 8 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 21% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[7]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L2C2S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cnc2c(c1)ccc1cccnc12"
},
{
"type": "NAME",
"value": "1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L2); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 21
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L2C2S1 (Figure S4)."
}
}
} | |||||
| reactions[8] | Record 9 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2-methyl-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 56% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[8]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L3C2S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-methyl-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L3); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 56
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L3C2S1 (Figure S4)."
}
}
} | |||||
| reactions[9] | Record 10 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2-chloro-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 65% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[9]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L4C2S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-chloro-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L4); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 65
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L4C2S1 (Figure S4)."
}
}
} | |||||
| reactions[10] | Record 11 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 4,5-diazafluoren-9-one SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 51% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[10]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L5C2S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "4,5-diazafluoren-9-one"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L5); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 51
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L5C2S1 (Figure S4)."
}
}
} | |||||
| reactions[11] | Record 12 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 55% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[11]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L6C2S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2c(c1)-c1ccccc1C21c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene]"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L6); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 55
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L6C2S1 (Figure S4)."
}
}
} | |||||
| reactions[12] | Record 13 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2,2'-bipyridine SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 27% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[12]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L1C3S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccn2)nc1"
},
{
"type": "NAME",
"value": "2,2'-bipyridine"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L1); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 27
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L1C3S1 (Figure S4)."
}
}
} | |||||
| reactions[13] | Record 14 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 55% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[13]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L2C3S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cnc2c(c1)ccc1cccnc12"
},
{
"type": "NAME",
"value": "1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L2); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 55
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L2C3S1 (Figure S4)."
}
}
} | |||||
| reactions[14] | Record 15 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2-methyl-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 76% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[14]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L3C3S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-methyl-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L3); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 76
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L3C3S1 (Figure S4)."
}
}
} | |||||
| reactions[15] | Record 16 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2-chloro-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 69% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[15]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L4C3S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-chloro-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L4); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 69
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L4C3S1 (Figure S4)."
}
}
} | |||||
| reactions[16] | Record 17 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 4,5-diazafluoren-9-one SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 77% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[16]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L5C3S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "4,5-diazafluoren-9-one"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L5); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 77
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L5C3S1 (Figure S4)."
}
}
} | |||||
| reactions[17] | Record 18 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 57% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[17]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L6C3S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2c(c1)-c1ccccc1C21c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene]"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L6); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 57
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L6C3S1 (Figure S4)."
}
}
} | |||||
| reactions[18] | Record 19 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2,2'-bipyridine SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 23% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[18]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L1C4S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccn2)nc1"
},
{
"type": "NAME",
"value": "2,2'-bipyridine"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L1); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 23
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L1C4S1 (Figure S4)."
}
}
} | |||||
| reactions[19] | Record 20 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 36% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[19]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L2C4S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cnc2c(c1)ccc1cccnc12"
},
{
"type": "NAME",
"value": "1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L2); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 36
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L2C4S1 (Figure S4)."
}
}
} | |||||
| reactions[20] | Record 21 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2-methyl-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 64% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[20]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L3C4S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-methyl-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L3); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 64
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L3C4S1 (Figure S4)."
}
}
} | |||||
| reactions[21] | Record 22 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 2-chloro-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 73% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[21]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L4C4S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-chloro-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L4); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 73
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L4C4S1 (Figure S4)."
}
}
} | |||||
| reactions[22] | Record 23 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: 4,5-diazafluoren-9-one SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 30% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[22]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L5C4S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "4,5-diazafluoren-9-one"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L5); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 30
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L5C4S1 (Figure S4)."
}
}
} | |||||
| reactions[23] | Record 24 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (2-(trifluoromethoxy)phenyl)boronic acid CATALYST: spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-2-(trifluoromethoxy)benzene · YIELD: 37% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[23]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S4",
"value": "L6C4S1"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "(2-(trifluoromethoxy)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2c(c1)-c1ccccc1C21c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene]"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L6); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccccc1OC(F)(F)F"
},
{
"type": "NAME",
"value": "1-fluoro-2-(trifluoromethoxy)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S4 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 37
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L6C4S1 (Figure S4)."
}
}
} | |||||
| reactions[24] | Record 25 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2,2'-bipyridine SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 3% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[24]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L1C1S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccn2)nc1"
},
{
"type": "NAME",
"value": "2,2'-bipyridine"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L1); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 3
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L1C1S2 (Figure S6)."
}
}
} | |||||
| reactions[25] | Record 26 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 13% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[25]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L2C1S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cnc2c(c1)ccc1cccnc12"
},
{
"type": "NAME",
"value": "1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L2); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 13
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L2C1S2 (Figure S6)."
}
}
} | |||||
| reactions[26] | Record 27 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2-methyl-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 21% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[26]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L3C1S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-methyl-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L3); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 21
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L3C1S2 (Figure S6)."
}
}
} | |||||
| reactions[27] | Record 28 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2-chloro-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 11% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[27]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L4C1S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-chloro-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L4); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 11
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L4C1S2 (Figure S6)."
}
}
} | |||||
| reactions[28] | Record 29 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 4,5-diazafluoren-9-one SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 2% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[28]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L5C1S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "4,5-diazafluoren-9-one"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L5); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 2
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L5C1S2 (Figure S6)."
}
}
} | |||||
| reactions[29] | Record 30 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 22% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[29]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L6C1S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2c(c1)-c1ccccc1C21c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene]"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L6); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 22
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L6C1S2 (Figure S6)."
}
}
} | |||||
| reactions[30] | Record 31 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2,2'-bipyridine SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 4% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[30]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L1C2S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccn2)nc1"
},
{
"type": "NAME",
"value": "2,2'-bipyridine"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L1); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 4
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L1C2S2 (Figure S6)."
}
}
} | |||||
| reactions[31] | Record 32 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 3% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[31]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L2C2S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cnc2c(c1)ccc1cccnc12"
},
{
"type": "NAME",
"value": "1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L2); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 3
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L2C2S2 (Figure S6)."
}
}
} | |||||
| reactions[32] | Record 33 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2-methyl-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 9% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[32]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L3C2S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-methyl-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L3); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 9
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L3C2S2 (Figure S6)."
}
}
} | |||||
| reactions[33] | Record 34 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2-chloro-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 53% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[33]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L4C2S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-chloro-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L4); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 53
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L4C2S2 (Figure S6)."
}
}
} | |||||
| reactions[34] | Record 35 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 4,5-diazafluoren-9-one SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 26% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[34]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L5C2S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "4,5-diazafluoren-9-one"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L5); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 26
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L5C2S2 (Figure S6)."
}
}
} | |||||
| reactions[35] | Record 36 | CATALYST: [Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 28% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[35]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L6C2S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1ccc(-c2cccc(-c3ccccn3)n2)nc1"
},
{
"type": "NAME",
"value": "[Pd(2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C2)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2c(c1)-c1ccccc1C21c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene]"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C2) and a second bidentate N,N-ligand (L6); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 28
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L6C2S2 (Figure S6)."
}
}
} | |||||
| reactions[36] | Record 37 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2,2'-bipyridine SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 8% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[36]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L1C3S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccn2)nc1"
},
{
"type": "NAME",
"value": "2,2'-bipyridine"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L1); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 8
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L1C3S2 (Figure S6)."
}
}
} | |||||
| reactions[37] | Record 38 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 11% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[37]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L2C3S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cnc2c(c1)ccc1cccnc12"
},
{
"type": "NAME",
"value": "1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L2); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 11
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L2C3S2 (Figure S6)."
}
}
} | |||||
| reactions[38] | Record 39 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2-methyl-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 12% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[38]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L3C3S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-methyl-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L3); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 12
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L3C3S2 (Figure S6)."
}
}
} | |||||
| reactions[39] | Record 40 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2-chloro-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 56% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[39]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L4C3S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-chloro-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L4); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 56
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L4C3S2 (Figure S6)."
}
}
} | |||||
| reactions[40] | Record 41 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 4,5-diazafluoren-9-one SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 46% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[40]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L5C3S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "4,5-diazafluoren-9-one"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L5); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 46
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L5C3S2 (Figure S6)."
}
}
} | |||||
| reactions[41] | Record 42 | CATALYST: [Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 22% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[41]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L6C3S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.CC(C)(C)c1ccnc(-c2cc(C(C)(C)C)cc(-c3cc(C(C)(C)C)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(4,4',4''-tri-tert-butyl-2,2':6',2''-terpyridine)(MeCN)](BF4)2 (complex C3)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2c(c1)-c1ccccc1C21c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene]"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C3) and a second bidentate N,N-ligand (L6); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 22
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L6C3S2 (Figure S6)."
}
}
} | |||||
| reactions[42] | Record 43 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2,2'-bipyridine SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 9% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[42]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L1C4S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccn2)nc1"
},
{
"type": "NAME",
"value": "2,2'-bipyridine"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L1); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 9
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L1C4S2 (Figure S6)."
}
}
} | |||||
| reactions[43] | Record 44 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 7% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[43]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L2C4S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cnc2c(c1)ccc1cccnc12"
},
{
"type": "NAME",
"value": "1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L2); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 7
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L2C4S2 (Figure S6)."
}
}
} | |||||
| reactions[44] | Record 45 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2-methyl-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 20% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[44]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L3C4S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Cc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-methyl-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L3); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 20
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L3C4S2 (Figure S6)."
}
}
} | |||||
| reactions[45] | Record 46 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 2-chloro-1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 25% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[45]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L4C4S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Clc1ccc2ccc3cccnc3c2n1"
},
{
"type": "NAME",
"value": "2-chloro-1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L4); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 25
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L4C4S2 (Figure S6)."
}
}
} | |||||
| reactions[46] | Record 47 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: 4,5-diazafluoren-9-one SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 17% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[46]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L5C4S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "O=C1c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "4,5-diazafluoren-9-one"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L5); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 17
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L5C4S2 (Figure S6)."
}
}
} | |||||
| reactions[47] | Record 48 | CATALYST: [Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (4-bromophenyl)boronic acid CATALYST: spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene] SOLVENT: acetonitrile | 60 CELSIUS | 1-bromo-4-fluorobenzene · YIELD: 24% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[47]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S6",
"value": "L6C4S2"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.COC(=O)c1ccnc(-c2cc(C(=O)OC)cc(-c3cc(C(=O)OC)ccn3)n2)c1.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2]"
},
{
"type": "NAME",
"value": "[Pd(trimethyl 2,2':6',2''-terpyridine-4,4',4''-tricarboxylate)(MeCN)](BF4)2 (complex C4)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "OB(O)c1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "(4-bromophenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc2c(c1)-c1ccccc1C21c2cccnc2-c2ncccc21"
},
{
"type": "NAME",
"value": "spiro[cyclopenta[2,1-b:3,4-b']dipyridine-5,9'-fluorene]"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C4) and a second bidentate N,N-ligand (L6); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "Fc1ccc(Br)cc1"
},
{
"type": "NAME",
"value": "1-bromo-4-fluorobenzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S6 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 24
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L6C4S2 (Figure S6)."
}
}
} | |||||
| reactions[48] | Record 49 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (3-(methylsulfonyl)phenyl)boronic acid CATALYST: 2,2'-bipyridine SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-3-(methylsulfonyl)benzene · YIELD: 2% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[48]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S5",
"value": "L1C1S3"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(=O)(=O)c1cccc(B(O)O)c1"
},
{
"type": "NAME",
"value": "(3-(methylsulfonyl)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1ccc(-c2ccccn2)nc1"
},
{
"type": "NAME",
"value": "2,2'-bipyridine"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L1); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(=O)(=O)c1cccc(F)c1"
},
{
"type": "NAME",
"value": "1-fluoro-3-(methylsulfonyl)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S5 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 2
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L1C1S3 (Figure S5)."
}
}
} | |||||
| reactions[49] | Record 50 | CATALYST: [Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1) REAGENT: Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)) REACTANT: (3-(methylsulfonyl)phenyl)boronic acid CATALYST: 1,10-phenanthroline SOLVENT: acetonitrile | 60 CELSIUS | 1-fluoro-3-(methylsulfonyl)benzene · YIELD: 4% [19F NMR] | 10.1021/jacs.5c11929 |
Decoded fields · reactions[49]Only fields present in the bytes are shown. Unrecognized fields and binary payloads are marked as omitted. {
"identifiers": [
{
"type": "CUSTOM",
"details": "Substrates.csv reaction code; well shown in SI Figure S5",
"value": "L2C1S3"
}
],
"inputs": {
"Pd-terpyridine complex": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N.F[B-](F)(F)F.F[B-](F)(F)F.[Pd+2].c1cc(-c2ncc[nH]2)nc(-c2ncc[nH]2)c1"
},
{
"type": "NAME",
"value": "[Pd(2,6-bis(1H-imidazol-2-yl)pyridine)(MeCN)](BF4)2 (complex C1)"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"Selectfluor": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "F[B-](F)(F)F.F[B-](F)(F)F.F[N+]12CC[N+](CCl)(CC1)CC2"
},
{
"type": "NAME",
"value": "Selectfluor (1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REAGENT"
}
]
},
"aryl boronic acid": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(=O)(=O)c1cccc(B(O)O)c1"
},
{
"type": "NAME",
"value": "(3-(methylsulfonyl)phenyl)boronic acid"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "amount not reported in the SI for the HTE screen"
}
},
"reaction_role": "REACTANT"
}
]
},
"bidentate ligand": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "c1cnc2c(c1)ccc1cccnc12"
},
{
"type": "NAME",
"value": "1,10-phenanthroline"
}
],
"amount": {
"unmeasured": {
"type": "CATALYTIC",
"details": "loading not reported in the SI for the HTE screen"
}
},
"reaction_role": "CATALYST"
}
]
},
"solvent": {
"components": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CC#N"
},
{
"type": "NAME",
"value": "acetonitrile"
}
],
"amount": {
"unmeasured": {
"type": "CUSTOM",
"details": "volume not reported in the SI for the HTE screen"
}
},
"reaction_role": "SOLVENT"
}
]
}
},
"setup": {
"vessel": {
"type": "VIAL",
"details": "1 mL clear glass shell vial, 8 x 30 mm (Analytical Sales 84001), oven-dried 120 C 24 h",
"material": {
"type": "GLASS"
},
"volume": {
"value": 1,
"units": "MILLILITER"
}
},
"is_automated": false,
"environment": {
"type": "GLOVE_BOX",
"details": "96-well aluminum reaction block (Analytical Sales 96973)"
}
},
"conditions": {
"temperature": {
"control": {
"type": "CUSTOM",
"details": "VP Scientific heating block with INKBIRD 741D controller"
},
"setpoint": {
"value": 60,
"units": "CELSIUS"
}
},
"pressure": {
"atmosphere": {
"type": "NITROGEN",
"details": "Reactions performed under nitrogen (SI General specifications)"
}
},
"stirring": {
"type": "STIR_BAR",
"details": "VP710C5-7A-CC tumble stirrer, parylene-coated stir bars VP712-1",
"rate": {
"rpm": 1000
}
}
},
"notes": {
"safety_notes": "Selectfluor is a strong oxidant/electrophilic fluorinating agent.",
"procedure_details": "HTE training-set screen (SI Section VI): heteroleptic Pd catalyst formed from a Pd-terpyridine complex (C1) and a second bidentate N,N-ligand (L2); aryl boronic acid + Selectfluor in acetonitrile (solvent per SI Section IX/X; HTE section does not restate it); 1 mL glass vials in a 96-well block, stirred 20 h at 60 C, then analyzed. The SI does not report HTE amounts, scale, concentration or Selectfluor/catalyst loadings, so no amounts are recorded. (The Section IX control scheme uses 10 mol% Pd complex, 10 mol% ligand, 2 equiv Selectfluor, MeCN, 60 C, 20 h, but is not stated to be the HTE condition.)"
},
"outcomes": [
{
"reaction_time": {
"value": 20,
"units": "HOUR"
},
"products": [
{
"identifiers": [
{
"type": "SMILES",
"value": "CS(=O)(=O)c1cccc(F)c1"
},
{
"type": "NAME",
"value": "1-fluoro-3-(methylsulfonyl)benzene"
}
],
"is_desired_product": true,
"measurements": [
{
"analysis_key": "19F NMR",
"type": "YIELD",
"details": "Yield from SI heatmap Figure S5 / Substrates.csv. The SI labels the value only as 'Yield (%)'; the HTE analysis method is not stated. The EDBO+ section states its data were 19F NMR yields vs 1-fluoro-4-(trifluoromethyl)benzene, and the HTE data were used to pretrain that model, so 19F NMR assay is assumed but not confirmed.",
"percentage": {
"value": 4
}
}
],
"reaction_role": "PRODUCT"
}
],
"analyses": {
"19F NMR": {
"type": "NMR_OTHER",
"details": "Analytical yield; method not explicitly stated for HTE (assumed quantitative 19F NMR of crude mixture with internal standard)."
}
}
}
],
"provenance": {
"doi": "10.1021/jacs.5c11929",
"publication_url": "https://doi.org/10.1021/jacs.5c11929",
"record_created": {
"time": {
"value": "2026-10-14T00:00:00Z"
},
"person": {
"name": "Tokens for Progress",
"email": "hello@tokensforprogress.org"
},
"details": "Curated from the SI by Tokens for Progress user @jordan with AI assistance (Claude). HTE well L2C1S3 (Figure S5)."
}
}
} | |||||