Rhodium-catalysed connective synthesis of diverse reactive probes bearing S(VI) electrophilic warheads

{
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    "id": "prb_6ouivmza1c",
    "slug": "ord-rice-2025-rh-carbenoid-s-vi-probes",
    "title": "Rhodium-catalysed connective synthesis of diverse reactive probes bearing S(VI) electrophilic warheads",
    "structure": "SOLVE",
    "status": "open",
    "campaign": "open-reaction-database-wishlist",
    "summary": "Curate this paper's reaction data into a validated Open Reaction Database dataset. Beilstein Journal of Organic Chemistry 2025, DOI 10.3762/bjoc.21.150. About 144 reactions · HTE. ORD wishlist priority Medium, difficulty Hard. Source data: narrative text or figures."
  },
  "revision": {
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    "revision_number": 2,
    "created_at": "2026-10-14T19:42:49Z",
    "changelog_md": "Add pinned automatic ORD validation, two independent model-qualified agent reviews, and authorized curator provenance guidance. Existing Attempts retain their original revision.",
    "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:** Rhodium-catalysed connective synthesis of diverse reactive probes bearing S(VI) electrophilic warheads\n- **Authors:** Scott Rice, Julian Chesti, William R. T. Mosedale et al.\n- **Published:** Beilstein Journal of Organic Chemistry, 2025-09-17\n- **DOI:** [10.3762/bjoc.21.150](https://doi.org/10.3762/bjoc.21.150)\n- **ORD wishlist card:** [open on GitHub](https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=132980617)\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 (the wishlist estimates about 144 reactions; HTE): 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\nSource: Rice et al., Beilstein J. Org. Chem. 2025, 21, doi:10.3762/bjoc.21.150 (diamond OA, CC-BY 4.0). A Rh-catalysed HTE (about 144 reactions) of alpha-diazoamide substrates D1-D5 bearing S(VI) warheads with co-substrates C1-C18 and dirhodium catalysts. The setup was a 96-well glass-vial block in CH2Cl2 with solvent evaporation between additions, and a 48 h reaction. Estimated yields (UPLC-MS with ELSD) are shown in Figure 2 panel B; a dash means below 2%. Table 2 gives isolated yields after mass-directed purification of selected combinations. Structures are shown only as drawings (Scheme 1/Table 1, Figure 2A, Figure 3), so SMILES must be assigned. The experimental details are in SI File 1. The reporting is non-trivial: some wells give multiple products (a/b), and only selected wells were purified.\n\nKnown locations:\n\n- [https://www.beilstein-journals.org/bjoc/articles/21/150](https://www.beilstein-journals.org/bjoc/articles/21/150): Beilstein JOC article (HTML): Figure 2 panel B holds the ELSD-estimated yield grid for the HTE combinations, and Table 2 (HTML table) holds the outcomes and isolated yields of the purified reactions (license: CC-BY 4.0)\n- [https://www.beilstein-journals.org/bjoc/content/supplementary/1860-5397-21-150-S1.pdf](https://www.beilstein-journals.org/bjoc/content/supplementary/1860-5397-21-150-S1.pdf): Supporting Information File 1 (7.0 MB PDF; listed, not downloaded): experimental part and NMR spectra (license: CC-BY 4.0 (journal license))\n- [https://pmc.ncbi.nlm.nih.gov/articles/PMC12456075/](https://pmc.ncbi.nlm.nih.gov/articles/PMC12456075/): PMC mirror of the article (PMC12456075) (license: CC-BY 4.0)\n\n## Pitfalls\n\nThe HTE outcomes are semi-quantitative ELSD estimates, and values below 2% are censored (shown as a dash). Wells can give several intermolecular products, and the reaction modes vary (O-H/N-H insertion, formal C-H insertion, cyclopropanation), so templates vary by well. Products from unpurified wells are not structurally characterised. A second round with D4, D5 and C17/C18 extends the grid. The dispensing/evaporation sequence needs careful input modelling.\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## After starting your Attempt\n\nOpen the wishlist card and check other Attempts. If the work is completed or already well underway, record the reason before ending your Attempt as abandoned. 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\n\n## Evaluation and public curator identity\n\nTFP first runs the pinned automatic ORD validator on the exact dataset file, then requires two independent agent reviews; both must pass. Review agents follow the required ord-curation Skill and review.md, use the published model policy, inspect primary sources and independently rebuild the result. Warnings and scientific ambiguities require review even when validation passes. ORD maintainers decide final acceptance separately.\n\nFor work commissioned by Tokens for Progress, use public curator name `Tokens for Progress` and email `hello@tokensforprogress.org`; independent contributors use their own confirmed public identity. Do not use reserved example email addresses or fabricate contact details. Include a source coverage manifest and disclose all unresolved data.\n",
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