Visible-Light-Mediated Photoredox Catalytic Hydro- and Heterotrifluoromethylation of Alkynes: Application and Mechanism

作者：Niu Tang, Songhua Chen, Chenghan Li, Peng Du, Weijun Yang, Renhua Qiu · 发表于：ACS Catalysis · 年份：2025 · DOI：10.1021/acscatal.5c02420 · 被引用次数：5 · 研究领域：Fluorine in Organic Chemistry、Inorganic Fluorides and Related Compounds、Radical Photochemical Reactions

A visible-light-induced hydro- and heterotrifluoromethylation, including iodo-, bromo-, thiol-, and seleno-trifluoromethylation, of alkynes is developed. Langlois reagent, CF 3 SO 2 Na, serves as CF 3 source and sole reductant by the action of photoredox catalysis under mild reaction conditions. This methodology provides facile access to a highly valuable set of CF 3 -containing molecules starting from readily available materials. The mechanistic studies confirm that the stereoenrichment of the trifluoromethylated aromatic alkenes is achieved through rapid photodynamic E/Z isomerization and that the trifluoromethylated alkyl alkenes proceed via stable intermediates to generate the thermodynamic products. The developed methodology could be applied in the high E/Z stereoselective synthesis of the vinylic CF 3 moiety.