{
  "source": "ORD Dataset Wishlist",
  "snapshot_date": "2026-09-25",
  "ord_wishlist_status_at_snapshot": "Available",
  "ord_wishlist_card": "https://github.com/orgs/open-reaction-database/projects/11?pane=issue&itemId=126570032",
  "ord_data_issue": null,
  "title": "Accessing Diverse Azole Carboxylic Acid Building Blocks via Mild C–H Carboxylation: Parallel, One-Pot Amide Couplings and Machine-Learning-Guided Substrate Scope Design",
  "doi": "10.1021/jacs.2c10557",
  "journal": "Journal of the American Chemical Society",
  "publication_date": "2022-12-09",
  "authors": [
    "Stephanie Felten",
    "Cyndi Qixin He",
    "Mark Weisel",
    "Michael Shevlin",
    "Marion H. Emmert"
  ],
  "article_open_access": {
    "status": "closed",
    "license": null
  },
  "dataset_size_estimate": null,
  "experiment_type": null,
  "ord_priority": null,
  "ord_difficulty": null,
  "source_data_kind": "unknown",
  "smiles_in_source": "unknown",
  "needs_author_contact": false,
  "data_locations": [
    {
      "url": "https://doi.org/10.1021/jacs.2c10557",
      "what": "JACS article and Supporting Information (scope, 24x12 parallel library, DFT)",
      "license": "ACS standard terms (closed-access article)"
    },
    {
      "url": "https://doi.org/10.26434/chemrxiv-2022-x1vmm",
      "what": "ChemRxiv preprint (Crossref has-preprint relation) and its SI",
      "license": "unknown (ChemRxiv item license not retrievable, 403)"
    }
  ],
  "notes": "Source: Felten et al., J. Am. Chem. Soc. 2022, doi:10.1021/jacs.2c10557 (Merck). A preprint exists at doi:10.26434/chemrxiv-2022-x1vmm. Chemistry: metal-free C-H carboxylation of azoles with CO2, mediated by silyl triflates, followed by one-pot amide coupling. Data to curate: (1) the ML-guided azole substrate scope; (2) the 24 x 12 parallel-synthesis library (about 288 reactions, 90% reported library success). Also covered are the low-pressure CO2-balloon variant, 13CO2 labeling and isocyanate electrophiles. First check the SI (ACS and/or ChemRxiv) for tabulated or spreadsheet results. The two-step one-pot sequence must be represented as a multi-step or sequential-addition procedure. The data format is not yet confirmed.",
  "verification_caveats": "One-pot two-step telescoped process (carboxylation, then amide coupling) needs careful encoding of addition order. Library outcomes may be reported as success/failure or LCMS purity, not yields. Gas reagent (CO2, some runs at pressure) must be captured."
}