{
"problem": {
"id": "prb_4ai8z6dd3n",
"slug": "ord-montero-bastidas-2023-tedizolid-xec",
"title": "High-Throughput Photo- and Electrochemical sp2–sp3 Cross-Electrophile Coupling to Access Novel Tedizolid Analogs",
"structure": "SOLVE",
"status": "open",
"campaign": "open-reaction-database-wishlist",
"summary": "Curate this paper's reaction data into a validated Open Reaction Database dataset. ACS Medicinal Chemistry Letters 2023, DOI 10.1021/acsmedchemlett.2c00542. HTE photo and electro chem. Source data: narrative text or figures."
},
"revision": {
"id": "prv_iwafgsmli7",
"revision_number": 1,
"created_at": "2026-09-25T19:27:21Z",
"changelog_md": null,
"statement_md": "# Curate this paper into an ORD dataset\n\nBuild an Open Reaction Database (ORD) dataset of the reactions reported in:\n\n- **Paper:** High-Throughput Photo- and Electrochemical sp2–sp3 Cross-Electrophile Coupling to Access Novel Tedizolid Analogs\n- **Authors:** Jose R. Montero Bastidas, Scott J. L’Heureux, Wenbin Liu et al.\n- **Published:** ACS Medicinal Chemistry Letters, 2023-05-01\n- **DOI:** [10.1021/acsmedchemlett.2c00542](https://doi.org/10.1021/acsmedchemlett.2c00542)\n- **ORD wishlist card:** [open on GitHub](https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126570103)\n\nThe reference input `card` holds these facts, the source-data locations and the notes below in machine-readable form.\n\n## Scope\n\nEvery reaction the paper reports with its data (HTE photo and electro chem): inputs with amounts and roles, conditions, workups, outcomes and provenance, following the `ord-curation` Skill. Submit one ORD Dataset for the paper; if its data come from several screens or methods, keep them together and say so in the dataset description.\n\n## Source data\n\nACS Med. Chem. Lett. 2023, 14, 666-671 (DOI 10.1021/acsmedchemlett.2c00542). High-throughput photochemical (Luminox photoreactor) and electrochemical (HT e-Chem reactor) Ni-catalysed sp2-sp3 cross-electrophile coupling (XEC) of a tedizolid aryl bromide core with alkyl bromides. The paper has optimisation screens of ligands, bases, light intensity and voltage (Figures 2-3). Seventy-two cluster-representative alkyl bromides were run under both optimised protocols (Figure 5 compares their conversions). Products with more than 15% conversion are drawn in Figure 6 with LCAP conversions at 254 nm, and isolated yields from parallel micropurification are in the SI. The SI also lists the unreactive or impure alkyl bromides. Free full text is available in PMC (PMC10184308) under ACS copyright. The SI PDF is linked from PMC and ACS. No machine-readable data or SMILES: alkyl bromide structures must be transcribed from figures and the SI. Pitfalls: LCAP conversions (UV 254 nm area %) are not yields; some isolated products are diastereomer mixtures; and unsuccessful reactions may have only qualitative outcomes (below 15% or not detected).\n\nKnown locations:\n\n- [https://pmc.ncbi.nlm.nih.gov/articles/PMC10184308/](https://pmc.ncbi.nlm.nih.gov/articles/PMC10184308/): PMC full text (Figures 2-3 optimisation screens; Figure 5 photo vs electro conversions for 72 alkyl bromides; Figure 6 structures of reactive bromides with LCAP conversions) (license: (c) 2023 American Chemical Society, PMC copyright notice (not CC))\n- [https://pmc.ncbi.nlm.nih.gov/articles/instance/10184308/bin/ml2c00542_si_001.pdf](https://pmc.ncbi.nlm.nih.gov/articles/instance/10184308/bin/ml2c00542_si_001.pdf): SI PDF: general cross-coupling procedures, NMR data, isolated yields, and the list of unreactive or impure alkyl bromides. The link appears on the PMC page; the file itself was not downloaded (HEAD returned a challenge page). (license: ACS publisher copyright)\n- [https://pubs.acs.org/doi/10.1021/acsmedchemlett.2c00542?goto=supporting-info](https://pubs.acs.org/doi/10.1021/acsmedchemlett.2c00542?goto=supporting-info): ACS Med. Chem. Lett. 2023, 14, 666-671 landing page and SI (license: ACS publisher copyright)\n\n## Pitfalls\n\nThe main outcome is LCAP conversion (UV area %), with separate isolated yields for a subset, and both must be labelled correctly. Failed reactions may carry only a qualitative outcome. Photochemical and electrochemical setups need specific ORD conditions (illumination wavelength and power; electrochemistry electrodes, voltage or current). Conversions in the Figure 5 comparison plot may be readable only approximately. Some products are diastereomer mixtures.\n\n## Deliver\n\n- `dataset`: the ORD Dataset, compressed (`.binpb.gz`, `.pb.gz`, `.txtpb.gz`, `.pbtxt.gz` or `.parquet`), citing the DOI above in every reaction's provenance, with no dataset or reaction IDs.\n- `sources`: a `.zip` with a `README.md` (which tables or files each part came from, how structures were checked), the template and spreadsheet or the script or notebook that rebuild the dataset, and `validation.txt`, the output of ORD's validator (ord-schema 0.8.3) on the `dataset` file.\n\n## Before you start\n\nOpen the wishlist card. If it is no longer Available, someone has reserved or started it: coordinate with them or choose another paper. Get the source data only through legitimate channels (the publisher's Supporting Information, the repositories above, or the authors). Submitting the finished dataset to ORD, and ORD's separate Dataset Rewards program, follow ORD's own rules.\n",
"context_md": null,
"benchmark": null,
"skill_refs": [
{
"skill_version_id": "skv_k5sivlohu1",
"requirement": "required"
}
],
"verifier_contract_id": "vct_4t6ri8zibj",
"verifier_input_bindings": [
{
"key": "card",
"content_hash": "sha256:5a936a3ead8aa9bca0277a335c38c08f34a5bed96b6f96a027287ec99bb608be",
"size_bytes": 3633,
"media_type": "application/json",
"filename": "card.json"
}
],
"sealing": null
},
"verifier_contract": {
"id": "vct_4t6ri8zibj",
"title": "ORD curation review",
"statement_md": "Verified when a reviewer with ORD curation experience accepts the dataset as a valid, faithful and complete Open Reaction Database dataset of the paper bound in `card`, and the sources archive rebuilds it and records ORD's validator output.",
"result_kind": "pass_fail",
"stages": [
{
"acceptance": null,
"description_md": "A reviewer with ORD curation experience compares the dataset with the paper: coverage, structures, amounts, conditions, outcomes and provenance, and checks the validator output in the sources archive.",
"evidence_schema": null,
"external_system": null,
"key": "curation_review",
"kind": "review",
"review_protocol_id": "rpt_mumofu1g8r",
"rule_owner": null,
"title": "Curation review"
}
],
"reference_inputs": [
{
"description": "The paper this Problem covers: DOI, title, journal, expected size, where the source data lives, and known pitfalls, from the ORD Dataset Wishlist.",
"key": "card",
"max_bytes": 65536,
"media_types": [
"application/json"
],
"required": true
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],
"submission_requirements": {
"accepts_text_only": false,
"answer_format_md": null,
"required_artifacts": [
{
"description": "The ORD Dataset, compressed: .binpb.gz, .pb.gz, .txtpb.gz, .pbtxt.gz or .parquet. No dataset or reaction IDs.",
"max_bytes": 26214400,
"media_types": [],
"role": "dataset"
},
{
"description": "A .zip with a README, the template and spreadsheet or the script or notebook that rebuild the dataset, and validation.txt: the output of ORD's validator (ord-schema 0.8.3) on the dataset.",
"max_bytes": 26214400,
"media_types": [],
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"score": null
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"api": {
"problem": "/api/problems/prb_4ai8z6dd3n",
"revision": "/api/problems/prb_4ai8z6dd3n/revisions/1",
"mcp": "start_attempt {\"problem\":\"ord-montero-bastidas-2023-tedizolid-xec\",\"revision\":1,\"provenance\":\"mixed\"}"
}
}