{
  "abstract": "Carbon-chain extension enables systematic modification of molecular frameworks, yet general two-carbon homologation of alcohols remains underdeveloped. Herein, we report a divergent two-carbon extension of primary, secondary, and tertiary alcohols through a radical–polar relay. Photocatalytic radical C–O bond cleavage merged with vinylsulfonium salt enabled a subsequent nucleophilic substitution to afford divergent two-carbon insertion products with oxygen-, nitrogen-, sulfur-, and carbon-based nucleophiles. The method tolerates alkenes, esters, carbamates, acetals, and complex molecular frameworks. Both two-carbon, and formal three-carbon homologation of alcohols are demonstrated. Intramolecular substitution provides substituted pyrrolidines or piperidine from amino alcohols. A quick access to fluspirilene, pimozide, and lidoflazine from 2,2-bis-4-fluorophenyl ethanol further demonstrated the synthetic utility.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry",
    "University of Hawai’i at Mānoa"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 3,
  "authors": [
    {
      "affs": [
        0,
        1
      ],
      "name": "Tiancen Bian"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Marcus A. Tius"
    },
    {
      "affs": [
        0,
        1
      ],
      "name": "Zuxiao Zhang",
      "orcid": "0000-0003-2365-6312"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/0zm56ca5xppw3.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15010493/v1",
  "fulltext_url": null,
  "id": "0zm56ca5xppw3",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010493/v1",
  "language": null,
  "licence": "CC-BY",
  "licence_label": "CC BY",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Radical Photochemical Reactions"
    ]
  ],
  "openalex": "W7221886633",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15010493/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-15",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/0zm56ca5xppw3.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:24Z",
      "native_id": "10.26434/chemrxiv.15010493",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010493/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Radical Photochemical Reactions",
      "subfield": "organic"
    }
  ],
  "title": "Divergent Two-Carbon Insertion of Alcohols",
  "title_text": "Divergent Two-Carbon Insertion of Alcohols",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:24Z",
  "url": "https://research.draconitic.com/paper/0zm56ca5xppw3",
  "venue": "ChemRxiv",
  "versions": []
}