4.8 Article

Selective C-F bond carboxylation of gem-difluoroalkenes with CO2 by photoredox/palladium dual catalysis

期刊

CHEMICAL SCIENCE
卷 10, 期 27, 页码 6721-6726

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9sc01336a

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资金

  1. Thousand Talents Plan Youth Program
  2. National Natural Science Foundation of China [21801131, 21871138]
  3. Natural Science Foundation of Jiangsu Province [BK20170992, BK20170984]
  4. Jiangsu Specially-Appointed Professor Plan

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The catalytic C-F bond carboxylation of organofluorines with CO2 gas remains a challenging problem in synthetic chemistry. Here, we describe a selective defluorinative carboxylation of gem-difluoroalkenes through photoredox/palladium dual catalysis. The C-F bond activation is enabled by single electron reduction through photoredox catalysis to generate a fluorovinyl radical, which subsequently participates in an unprecedented palladium-catalyzed carboxylation. This novel C-F functionalization proved applicable to a wide range of substituted gem-difluoroalkenes, providing a rapid access to valuable alpha-fluoroacrylic acids.

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