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.
Authors
- Yu‐Cheng Gu (ORCID: https://orcid.org/0000-0002-6400-6167)
- Tao Shu (ORCID: https://orcid.org/0000-0003-0079-3832)
- Fuyan Xiao
- Cheng‐Pan Zhang (ORCID: https://orcid.org/0000-0002-2803-4611)
- Ming Xu (ORCID: https://orcid.org/0000-0003-2151-2980)
Institutions
- Wuhan University of Technology (CN)
- Syngenta (United Kingdom) (GB)
- Syngenta (Switzerland) (CH)
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