Photoredox Catalytic Defluoroalkylation of <i>gem</i>-Difluoroalkenes with Secondary <i>N</i>-Alkylanilines via C–F/C–H Coupling

To provide fluorinated allylamines, a visible-light photocatalytic C-F/C-H coupling of easily accessible <i>gem</i>-difluoroalkenes and secondary <i>N</i>-alkylanilines was described. The protocol proceeded under mild conditions, with excellent functional group compatibility and a broad scope including complex natural product derivatives, thus providing a green method for the preparation of high-value functionalized monofluoroalkenes. Mechanistic studies elucidated a photoredox catalyzed radical-radical coupling pathway.

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Publication Details

Journal
Organic Letters
Published
2024-12-23
DOI
https://doi.org/10.1021/acs.orglett.4c04432
Citations
2
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.42

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article

Photoredox Catalytic Defluoroalkylation of gem-Difluoroalkenes with Secondary N-Alkylanilines via C–F/C–H Coupling

Wengang Xu, Congjian Xia, Yifan Liu, Hai Hu et al.
2 citations
Organic Letters
Fluorine in Organic Chemistry
0.42
article

Photoredox Catalytic Defluoroalkylation of gem-Difluoroalkenes with Secondary N-Alkylanilines via C–F/C–H Coupling

Wengang Xu, Congjian Xia, Yifan Liu, Hai Hu, Mingbo Wu, Guoqiang Xu, Baokai Yang
article en
2 citations

Abstract

To provide fluorinated allylamines, a visible-light photocatalytic C-F/C-H coupling of easily accessible <i>gem</i>-difluoroalkenes and secondary <i>N</i>-alkylanilines was described. The protocol proceeded under mild conditions, with excellent functional group compatibility and a broad scope including complex natural product derivatives, thus providing a green method for the preparation of high-value functionalized monofluoroalkenes. Mechanistic studies elucidated a photoredox catalyzed radical-radical coupling pathway.

Organic LettersVol. 27(1)
Qingdao Institute of Bioenergy and Bioprocess Technology (CN), China University of Petroleum, East China (CN)
National Natural Science Foundation of China, China Postdoctoral Science Foundation, Natural Science Foundation of Shandong Province, Major Scientific and Technological Innovation Project of Shandong Province
Openalex Percentile: Top 40%
Fluorine in Organic Chemistry
0.42
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