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PreprintCC BYChemRxiv

Divergent Two-Carbon Insertion of Alcohols

  • Tiancen Bian1,2
  • Marcus A. Tius1,2
  • Zuxiao Zhang1,2
  1. 1Department of Chemistry
  2. 2University of Hawai’i at Mānoa
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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.

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Cite

BibTeXRIS
BibTeX
@misc{bian2026divergent,
  title = {{Divergent Two-Carbon Insertion of Alcohols}},
  author = {Tiancen Bian and Marcus A. Tius and Zuxiao Zhang},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010493/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010493/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Divergent Two-Carbon Insertion of Alcohols
AU  - Tiancen Bian
AU  - Marcus A. Tius
AU  - Zuxiao Zhang
PY  - 2026
DA  - 2026/10/15
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010493/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010493/v1
AB  - 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.
ER  -