{
  "problem": {
    "id": "prb_2xrnydqq5z",
    "slug": "ord-ickes-2025-pd-n-arylation-ligands",
    "title": "Leveraging Data Science to Elucidate Ligand Features for Pd-Catalyzed Enantioretentive N-Arylations of Cyclic α-Substituted Amines in Aqueous Media",
    "summary": "Curate this paper's reaction data into a validated Open Reaction Database dataset. JACS 2025, DOI 10.1021/jacs.5c07224. About 121 reactions. ORD wishlist priority High, difficulty Easy. Source data: a spreadsheet or CSV in the Supporting Information.",
    "structure": "SOLVE"
  },
  "revision": {
    "sealing": null,
    "id": "prv_f27k7ghbqk",
    "problem_id": "prb_2xrnydqq5z",
    "revision_number": 1,
    "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:** Leveraging Data Science to Elucidate Ligand Features for Pd-Catalyzed Enantioretentive N-Arylations of Cyclic α-Substituted Amines in Aqueous Media\n- **Authors:** Andrew R. Ickes, Jordan P. Liles, Niginia Borlinghaus et al.\n- **Published:** JACS, 2025-07-30\n- **DOI:** [10.1021/jacs.5c07224](https://doi.org/10.1021/jacs.5c07224)\n- **ORD wishlist card:** [open on GitHub](https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126794871)\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 121 reactions): 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: J. Am. Chem. Soc. 2025, DOI 10.1021/jacs.5c07224 (Pd-catalysed enantioretentive N-arylation of cyclic alpha-substituted amines in aqueous media, about 121 reactions). According to the dataset wishlist, the reaction data is in a spreadsheet in the Supporting Information and includes SMILES. Tip from ORD curators: the calculated ligand parameters can be added to the ligand components as ORD 'features', ideally one feature per spreadsheet column. The article is not open access. Download the SI from the publisher and cite the paper DOI in the dataset. Do not redistribute the SI file itself.\n\nKnown locations:\n\n- [https://doi.org/10.1021/jacs.5c07224](https://doi.org/10.1021/jacs.5c07224): JACS article and Supporting Information (ORD curators report a spreadsheet with SMILES plus calculated ligand parameters) (license: ACS publisher licence (Crossref lists only stm-asf policy URLs; article closed access); SI licence unknown)\n\n## Pitfalls\n\nThe reaction conditions (the aqueous or surfactant medium, base, Pd source and temperature) may be given only in the SI text, not in the spreadsheet, and must be merged in by hand. Chiral amine stereochemistry must be kept in the SMILES, and enantiospecificity or ee outcomes need correct ORD measurement types. Ligand descriptor features are optional but add columns to check. We could not confirm the SI contents here (ACS blocks automated access).\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,
    "verifier_contract_id": "vct_4t6ri8zibj",
    "verifier_input_bindings": [
      {
        "key": "card",
        "content_hash": "sha256:09fe38776f4fd447e54a300e697431e89b1ef17c3bdf2308545678e7c04ab657",
        "size_bytes": 2531,
        "media_type": "application/json",
        "filename": "card.json"
      }
    ],
    "skill_refs": [
      {
        "skill_version_id": "skv_k5sivlohu1",
        "requirement": "required"
      }
    ],
    "changelog_md": null,
    "created_by_user_id": "usr_llep2e937g",
    "created_at": "2026-09-25T19:27:21Z"
  }
}