Visible-Light-Driven ( <i>E</i> )-β-Trifluoromethylation of Enamides via <i>In Situ</i> Generated Sulfur(VI) Photosensitizers

We report an autoinductive, visible-light-mediated (<i>E</i>)-β-trifluoromethylation of enamides using sodium trifluoromethanesulfinate. This protocol eliminates exogenous catalysts by leveraging an <i>in situ</i> generated pentacoordinate sulfur(VI) species as the photosensitizer. Characterized by mild conditions and broad substrate compatibility, the method exhibits promising scalability, as evidenced by a gram-scale continuous-flow synthesis. This oxidant- and catalyst-free strategy provides a robust, scalable paradigm for accessing valuable trifluoromethylated building blocks.

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Publication Details

Journal
Organic Letters
Published
2026-03-17
DOI
https://doi.org/10.1021/acs.orglett.6c00782
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
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article

Visible-Light-Driven ( E )-β-Trifluoromethylation of Enamides via In Situ Generated Sulfur(VI) Photosensitizers

Caiwen Wan, Yong Li, Dingfeng Yang, Ruolan Leng et al.
Organic Letters
Fluorine in Organic Chemistry
article

Visible-Light-Driven ( E )-β-Trifluoromethylation of Enamides via In Situ Generated Sulfur(VI) Photosensitizers

Caiwen Wan, Yong Li, Dingfeng Yang, Ruolan Leng, Yuanxue Yi, Yixi Bao, Changtong Shao, Rui Yang, Jie Gao
article en

Abstract

We report an autoinductive, visible-light-mediated (<i>E</i>)-β-trifluoromethylation of enamides using sodium trifluoromethanesulfinate. This protocol eliminates exogenous catalysts by leveraging an <i>in situ</i> generated pentacoordinate sulfur(VI) species as the photosensitizer. Characterized by mild conditions and broad substrate compatibility, the method exhibits promising scalability, as evidenced by a gram-scale continuous-flow synthesis. This oxidant- and catalyst-free strategy provides a robust, scalable paradigm for accessing valuable trifluoromethylated building blocks.

Organic LettersVol. 28(12)
Chongqing University (CN), Dalian Medical University (CN), Second Affiliated Hospital of Chongqing Medical University (CN), Chongqing University of Education (CN), Precision Research (United States) (US), Chongqing University of Technology (CN), Chongqing Medical University (CN)
Openalex Percentile: Top 17%
Fluorine in Organic Chemistry
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