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Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis

The catalytic C–F bond carboxylation of organofluorines with CO(2) 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 ele...

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Detalles Bibliográficos
Autores principales: Zhu, Chuan, Zhang, Yu-Feng, Liu, Ze-Yao, Zhou, Lu, Liu, Haidong, Feng, Chao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6625485/
https://www.ncbi.nlm.nih.gov/pubmed/31367327
http://dx.doi.org/10.1039/c9sc01336a
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author Zhu, Chuan
Zhang, Yu-Feng
Liu, Ze-Yao
Zhou, Lu
Liu, Haidong
Feng, Chao
author_facet Zhu, Chuan
Zhang, Yu-Feng
Liu, Ze-Yao
Zhou, Lu
Liu, Haidong
Feng, Chao
author_sort Zhu, Chuan
collection PubMed
description The catalytic C–F bond carboxylation of organofluorines with CO(2) 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 α-fluoroacrylic acids.
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spelling pubmed-66254852019-07-31 Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis Zhu, Chuan Zhang, Yu-Feng Liu, Ze-Yao Zhou, Lu Liu, Haidong Feng, Chao Chem Sci Chemistry The catalytic C–F bond carboxylation of organofluorines with CO(2) 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 α-fluoroacrylic acids. Royal Society of Chemistry 2019-05-28 /pmc/articles/PMC6625485/ /pubmed/31367327 http://dx.doi.org/10.1039/c9sc01336a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Zhu, Chuan
Zhang, Yu-Feng
Liu, Ze-Yao
Zhou, Lu
Liu, Haidong
Feng, Chao
Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis
title Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis
title_full Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis
title_fullStr Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis
title_full_unstemmed Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis
title_short Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis
title_sort selective c–f bond carboxylation of gem-difluoroalkenes with co(2) by photoredox/palladium dual catalysis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6625485/
https://www.ncbi.nlm.nih.gov/pubmed/31367327
http://dx.doi.org/10.1039/c9sc01336a
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