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

ABSTRACT: 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 ?-fluoroacrylic acids.

SUBMITTER: Zhu C

PROVIDER: S-EPMC6625485 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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

Zhu Chuan C Zhang Yu-Feng YF Liu Ze-Yao ZY Zhou Lu L Liu Haidong H Feng Chao C

Chemical science 20190528 27

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 fu ...[more]

PMID: 31367327

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