Merging Directed C–H Activations with High-Throughput Experimentation: Development of Iridium-Catalyzed C–H Aminations Applicable to Late-Stage Functionalization

{
  "problem": {
    "id": "prb_kbxa45q3ev",
    "slug": "ord-weis-2022-ir-ch-amination-hte",
    "title": "Merging Directed C–H Activations with High-Throughput Experimentation: Development of Iridium-Catalyzed C–H Aminations Applicable to Late-Stage Functionalization",
    "structure": "SOLVE",
    "status": "open",
    "campaign": "open-reaction-database-wishlist",
    "summary": "Curate this paper's reaction data into a validated Open Reaction Database dataset. JACS Au 2022, DOI 10.1021/jacsau.2c00039. About 300 reactions · HTE. Source data: tables in the Supporting Information PDF."
  },
  "revision": {
    "id": "prv_wbzokqynvy",
    "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:** Merging Directed C–H Activations with High-Throughput Experimentation: Development of Iridium-Catalyzed C–H Aminations Applicable to Late-Stage Functionalization\n- **Authors:** Erik Weis, Maria C. Johansson, Maria C. Johansson et al.\n- **Published:** JACS Au, 2022-04-13\n- **DOI:** [10.1021/jacsau.2c00039](https://doi.org/10.1021/jacsau.2c00039)\n- **ORD wishlist card:** [open on GitHub](https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126569968)\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 300 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\nIr-catalysed directed C-H amination HTE from Weis et al., JACS Au 2022 (doi:10.1021/jacsau.2c00039), an open-access CC BY 4.0 article also in PMC (PMC9088304). About 300 reactions run as single 96-well plate screens: initial condition optimisation, then a directing-group informer library of 48 substrates tested in DCE, CPME, EtOAc and NMP with [Cp*Ir(H2O)3]SO4, then late-stage functionalisation examples. Conversions, including for unproductive substrates, are reported in the Supporting Information PDF (about 17 MB). Structures are drawn, not given as SMILES, so each substrate, product and directing group must be converted to SMILES and checked. Outcomes are mostly LC conversions, with isolated yields for selected products. The ORD Dataset must cite the paper DOI.\n\nKnown locations:\n\n- [https://www.ebi.ac.uk/europepmc/webservices/rest/PMC9088304/fullTextXML](https://www.ebi.ac.uk/europepmc/webservices/rest/PMC9088304/fullTextXML): Full text (PMC9088304) under CC BY 4.0; states that the complete list of conversions, including unproductive substrates, is in the SI (license: CC-BY-4.0 (article))\n- [https://pmc.ncbi.nlm.nih.gov/articles/PMC9088304/](https://pmc.ncbi.nlm.nih.gov/articles/PMC9088304/): SI PDF au2c00039_si_001.pdf (about 17 MB per PMC metadata; not downloaded) with plate screens and conversion tables (license: Distributed with the CC BY 4.0 article; SI license not separately stated)\n- [https://doi.org/10.26434/chemrxiv-2021-vp0kl](https://doi.org/10.26434/chemrxiv-2021-vp0kl): ChemRxiv preprint (site blocked automated access) (license: unknown)\n\n## Pitfalls\n\nMix of screening conversions (LC area-based) and isolated yields. Structures must be transcribed from images. Plate layouts are spread across many single-plate figures. Regioisomer outcomes are reported for some substrates.\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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    "result_kind": "pass_fail",
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        "description_md": "Parse every reaction with ord-schema 0.8.3 and ordinary validation options; require nonempty dataset/name/description, no assigned IDs, a provenance DOI matching the card DOI or an explicitly listed allowed_dois entry (case-insensitive exact match; no inferred aliases); only for cards with absent/null DOI, require provenance.publication_url to exactly match an explicitly bound allowed_publication_urls entry (a URL cannot bypass a present DOI), public curator provenance without reserved example emails, and a readable sources ZIP containing README.md and validation.txt. Record warnings for review; warnings alone do not fail. Does not execute supplied code or certify scientific correctness. Resource envelope exhaustion is inconclusive.",
        "evidence_schema": null,
        "external_system": null,
        "key": "ord_validation",
        "kind": "sandbox",
        "review_protocol_id": null,
        "rule_owner": null,
        "title": "Automatic ORD validation"
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      {
        "acceptance": null,
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        "evidence_schema": null,
        "external_system": null,
        "key": "curation_review",
        "kind": "review",
        "review_protocol_id": "rpt_lghn4j4ulb",
        "rule_owner": null,
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}