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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...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2019
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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. |
format | Online Article Text |
id | pubmed-6625485 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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
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title_full | Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis
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title_fullStr | Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis
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title_full_unstemmed | Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis
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title_short | Selective C–F bond carboxylation of gem-difluoroalkenes with CO(2) by photoredox/palladium dual catalysis
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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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