{
  "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=126570103",
  "ord_data_issue": null,
  "title": "High-Throughput Photo- and Electrochemical sp2–sp3 Cross-Electrophile Coupling to Access Novel Tedizolid Analogs",
  "doi": "10.1021/acsmedchemlett.2c00542",
  "journal": "ACS Medicinal Chemistry Letters",
  "publication_date": "2023-05-01",
  "authors": [
    "Jose R. Montero Bastidas",
    "Scott J. L’Heureux",
    "Wenbin Liu",
    "Ken Chi Lik Lee",
    "Abdellatif El Marrouni"
  ],
  "article_open_access": {
    "status": "green",
    "license": null
  },
  "dataset_size_estimate": null,
  "experiment_type": "HTE photo and electro chem",
  "ord_priority": null,
  "ord_difficulty": null,
  "source_data_kind": "narrative_or_figures",
  "smiles_in_source": "no",
  "needs_author_contact": false,
  "data_locations": [
    {
      "url": "https://pmc.ncbi.nlm.nih.gov/articles/PMC10184308/",
      "what": "PMC full text (Figures 2-3 optimisation screens; Figure 5 photo vs electro conversions for 72 alkyl bromides; Figure 6 structures of reactive bromides with LCAP conversions)",
      "license": "(c) 2023 American Chemical Society, PMC copyright notice (not CC)"
    },
    {
      "url": "https://pmc.ncbi.nlm.nih.gov/articles/instance/10184308/bin/ml2c00542_si_001.pdf",
      "what": "SI PDF: general cross-coupling procedures, NMR data, isolated yields, and the list of unreactive or impure alkyl bromides. The link appears on the PMC page; the file itself was not downloaded (HEAD returned a challenge page).",
      "license": "ACS publisher copyright"
    },
    {
      "url": "https://pubs.acs.org/doi/10.1021/acsmedchemlett.2c00542?goto=supporting-info",
      "what": "ACS Med. Chem. Lett. 2023, 14, 666-671 landing page and SI",
      "license": "ACS publisher copyright"
    }
  ],
  "notes": "ACS Med. Chem. Lett. 2023, 14, 666-671 (DOI 10.1021/acsmedchemlett.2c00542). High-throughput photochemical (Luminox photoreactor) and electrochemical (HT e-Chem reactor) Ni-catalysed sp2-sp3 cross-electrophile coupling (XEC) of a tedizolid aryl bromide core with alkyl bromides. The paper has optimisation screens of ligands, bases, light intensity and voltage (Figures 2-3). Seventy-two cluster-representative alkyl bromides were run under both optimised protocols (Figure 5 compares their conversions). Products with more than 15% conversion are drawn in Figure 6 with LCAP conversions at 254 nm, and isolated yields from parallel micropurification are in the SI. The SI also lists the unreactive or impure alkyl bromides. Free full text is available in PMC (PMC10184308) under ACS copyright. The SI PDF is linked from PMC and ACS. No machine-readable data or SMILES: alkyl bromide structures must be transcribed from figures and the SI. Pitfalls: LCAP conversions (UV 254 nm area %) are not yields; some isolated products are diastereomer mixtures; and unsuccessful reactions may have only qualitative outcomes (below 15% or not detected).",
  "verification_caveats": "The main outcome is LCAP conversion (UV area %), with separate isolated yields for a subset, and both must be labelled correctly. Failed reactions may carry only a qualitative outcome. Photochemical and electrochemical setups need specific ORD conditions (illumination wavelength and power; electrochemistry electrodes, voltage or current). Conversions in the Figure 5 comparison plot may be readable only approximately. Some products are diastereomer mixtures."
}