{
"problem": {
"id": "prb_lclat1owdv",
"slug": "ord-kang-2021-cross-ullmann-biheteroaryl",
"title": "A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates",
"structure": "SOLVE",
"status": "open",
"campaign": "open-reaction-database-wishlist",
"summary": "Curate this paper's reaction data into a validated Open Reaction Database dataset. JACS 2021, DOI 10.1021/jacs.1c10907. Source data: tables in the Supporting Information PDF."
},
"revision": {
"id": "prv_3j47drcvpb",
"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:** A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates\n- **Authors:** Kai Kang, Nathan L. Loud, Tarah A. DiBenedetto et al.\n- **Published:** JACS, 2021-12-17\n- **DOI:** [10.1021/jacs.1c10907](https://doi.org/10.1021/jacs.1c10907)\n- **ORD wishlist card:** [open on GitHub](https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126570058)\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: 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\nThis paper describes a Ni/Pd multimetallic cross-Ullmann coupling of heteroaryl halides with heteroaryl triflates (JACS 2021). An author manuscript is free on PMC (PMC9007723), and the SI PDF (about 23 MB) is on the ACS figshare mirror, labelled CC BY-NC 4.0. Content to curate: Table 1 optimisation (0.25 mmol, calibrated GC yields; more selectivity data in SI Table S6); 62 scope examples with isolated yields; and a 96-well array of 8 triflates x 12 halides at 10 umol scale with toolbox and optimisation plates. Pitfalls: plate results are heatmaps of product/internal-standard ratios, which the authors say should not be compared across coupling partners, and the numbers may exist only as colours. Structures appear only as drawings or names, so SMILES must be derived. The SI PDF is large.\n\nKnown locations:\n\n- [https://pmc.ncbi.nlm.nih.gov/articles/PMC9007723/](https://pmc.ncbi.nlm.nih.gov/articles/PMC9007723/): Author manuscript full text (Table 1 optimisation, scope schemes, Figure 1 96-well heatmaps of Pdt/IS ratios) (license: NIH public-access author manuscript (not CC-licensed))\n- [https://acs.figshare.com/articles/journal_contribution/A_General_Multimetallic_Cross-Ullmann_Biheteroaryl_Synthesis_from_Heteroaryl_Halides_and_Heteroaryl_Triflates/17263772](https://acs.figshare.com/articles/journal_contribution/A_General_Multimetallic_Cross-Ullmann_Biheteroaryl_Synthesis_from_Heteroaryl_Halides_and_Heteroaryl_Triflates/17263772): SI PDF ja1c10907_si_001.pdf (about 23 MB; listed only, not downloaded): procedures, Table S6, characterisation, plate details (license: CC BY-NC 4.0 as labelled on the ACS figshare mirror)\n- [https://pmc.ncbi.nlm.nih.gov/articles/instance/9007723/bin/NIHMS1790236-supplement-supplementals.pdf](https://pmc.ncbi.nlm.nih.gov/articles/instance/9007723/bin/NIHMS1790236-supplement-supplementals.pdf): PMC copy of the supplementary PDF (license: unknown)\n- [https://doi.org/10.1021/jacs.1c10907](https://doi.org/10.1021/jacs.1c10907): Publisher version of the article (JACS 2021) (license: closed (ACS))\n\n## Pitfalls\n\nThere are several templates: an optimisation table, isolated-yield scope and HTE plates with Pdt/IS ratios. These probably belong in separate datasets or need clearly distinct outcome types. Plate outcomes are relative ratios rather than yields, and some may be recoverable only as heatmap colours. SMILES must be derived from drawn structures or names. Reactions are multimetallic (Ni and Pd catalysts, ligands, Zn reductant, KF/KBr additive) and need careful role assignment.\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:b4427ffd3ac2f5eb9221d2c316e27114d8dc70be61380eecd1c768e8eb065c13",
"size_bytes": 3275,
"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
}
],
"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
},
"api": {
"problem": "/api/problems/prb_lclat1owdv",
"revision": "/api/problems/prb_lclat1owdv/revisions/1",
"mcp": "start_attempt {\"problem\":\"ord-kang-2021-cross-ullmann-biheteroaryl\",\"revision\":1,\"provenance\":\"mixed\"}"
}
}