Copper-Mediated Photoinduced Trifluoromethylation of Arylsulfonium Salts with Yagupolskii–Umemoto Reagent

The copper-mediated, visible-light-induced trifluoromethylation of arylsulfonium salts using the Yagupolskii-Umemoto reagent as the trifluoromethyl source is described. This reaction allowed the convenient and efficient synthesis of CF<sub>3</sub>-containing arenes from different sulfonium salts under mild conditions, featuring excellent chemoselectivity, good functional group compatibility, and a broad range of substrates. Mechanistically, the present reductive trifluoromethylation likely involves the formation of a key [CuCF<sub>3</sub>] intermediate from the Yagupolskii-Umemoto reagent and its subsequent reduction and cross-coupling of an arylsulfonium salt. This transformation represents the first cross-coupling of two electrophilic sulfonium-based reagents and enables the late-stage functionalization of structurally diversified drug molecules.

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Publication Details

Journal
Organic Letters
Published
2025-11-25
DOI
https://doi.org/10.1021/acs.orglett.5c04518
Citations
2
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
1.58
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article

Copper-Mediated Photoinduced Trifluoromethylation of Arylsulfonium Salts with Yagupolskii–Umemoto Reagent

Yu‐Cheng Gu, Tao Shu, Fuyan Xiao, Cheng‐Pan Zhang et al.
2 citations
Organic Letters
Fluorine in Organic Chemistry
1.58
article

Copper-Mediated Photoinduced Trifluoromethylation of Arylsulfonium Salts with Yagupolskii–Umemoto Reagent

Yu‐Cheng Gu, Tao Shu, Fuyan Xiao, Cheng‐Pan Zhang, Ming Xu
article en
2 citations

Abstract

The copper-mediated, visible-light-induced trifluoromethylation of arylsulfonium salts using the Yagupolskii-Umemoto reagent as the trifluoromethyl source is described. This reaction allowed the convenient and efficient synthesis of CF<sub>3</sub>-containing arenes from different sulfonium salts under mild conditions, featuring excellent chemoselectivity, good functional group compatibility, and a broad range of substrates. Mechanistically, the present reductive trifluoromethylation likely involves the formation of a key [CuCF<sub>3</sub>] intermediate from the Yagupolskii-Umemoto reagent and its subsequent reduction and cross-coupling of an arylsulfonium salt. This transformation represents the first cross-coupling of two electrophilic sulfonium-based reagents and enables the late-stage functionalization of structurally diversified drug molecules.

Organic LettersVol. 27(49)
Wuhan University of Technology (CN), Syngenta (United Kingdom) (GB), Syngenta (Switzerland) (CH)
Openalex Percentile: Top 14%
Fluorine in Organic Chemistry
1.58
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