Cu Oxamate-Promoted Cross-Coupling of α-Branched Amines and Complex Aryl Halides: Investigating Ligand Function through Data Science

{
  "problem": {
    "id": "prb_jssswvblpr",
    "slug": "ord-matthews-2023-cu-oxamate-amine-arylation",
    "title": "Cu Oxamate-Promoted Cross-Coupling of α-Branched Amines and Complex Aryl Halides: Investigating Ligand Function through Data Science",
    "structure": "SOLVE",
    "status": "open",
    "campaign": "open-reaction-database-wishlist",
    "summary": "Curate this paper's reaction data into a validated Open Reaction Database dataset. ACS Catalysis 2023, DOI 10.1021/acscatal.3c04566. About 300 reactions · HTE. ORD wishlist priority Medium, difficulty Hard. Source data: tables in the Supporting Information PDF."
  },
  "revision": {
    "id": "prv_n6t9y0eb74",
    "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:** Cu Oxamate-Promoted Cross-Coupling of α-Branched Amines and Complex Aryl Halides: Investigating Ligand Function through Data Science\n- **Authors:** Adrian D. Matthews, Ellyn Peters, John S. Debenham et al.\n- **Published:** ACS Catalysis, 2023-12-05\n- **DOI:** [10.1021/acscatal.3c04566](https://doi.org/10.1021/acscatal.3c04566)\n- **ORD wishlist card:** [open on GitHub](https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126851437)\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\nACS Catalysis 2023 (DOI 10.1021/acscatal.3c04566), closed access. About 300 high-throughput experiments on copper/oxamate-promoted C-N cross-coupling of alpha-branched amines with complex aryl halides, used in a data-science study of ligand function. The data is in tables in the SI PDF. SMILES must be determined for the 25 oxamate ligands, and possibly for the complex aryl halide and amine partners. The publisher site blocks automated access, so contributors need to download the SI themselves. No repository deposit was found.\n\nKnown locations:\n\n- [https://doi.org/10.1021/acscatal.3c04566](https://doi.org/10.1021/acscatal.3c04566): Article and SI (per the board notes, ~300 HTE reactions in SI tables). The publisher site blocks automated access, so the SI was not inspected. No DataCite or GitHub deposit was found. (license: Closed article (Crossref lists only publisher TDM/STM policy URLs); SI copyright publisher)\n\n## Pitfalls\n\nLigand identities must be converted from drawn structures or codes to SMILES and cross-checked. Complex, drug-like aryl halides raise the risk of SMILES errors. The outcome metric (assay yield vs LC area%) and the HTE plate conditions (scale, solvent, base, Cu source, temperature) must be taken from the SI.\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,
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        "skill_version_id": "skv_k5sivlohu1",
        "requirement": "required"
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    "verifier_contract_id": "vct_4t6ri8zibj",
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        "size_bytes": 2366,
        "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": [
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        "required": true
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    "submission_requirements": {
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      "required_artifacts": [
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          "max_bytes": 26214400,
          "media_types": [],
          "role": "dataset"
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          "max_bytes": 26214400,
          "media_types": [],
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    "revision": "/api/problems/prb_jssswvblpr/revisions/1",
    "mcp": "start_attempt {\"problem\":\"ord-matthews-2023-cu-oxamate-amine-arylation\",\"revision\":1,\"provenance\":\"mixed\"}"
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