Light-Induced Radical C(sp2)-H Trifluorovinylation of (Hetero)arenes with a Trifluorovinyl Iodine(III) Reagent (TrFVI).

Trifluorovinyl group is an emerging and valuable motif in drug discovery and material science, especially in polymer-related researches. However, the practical and efficient synthesis of trifluorovinylated compounds with broad structural diversity still remains a challenging task. Herein, we report the scalable synthesis of a trifluorovinyl hypervalent iodine(III) reagent, ArI(CF ═ CF2)OTf (TrFVI), from a bulk chemical, HFC-134a. The first C(sp2)─H trifluorovinylation of (hetero)arenes is achieved using TrFVI reagent via photoredox catalysis, which shows good functional group compatibility. Furthermore, late-stage trifluorovinylation of highly modified substrates, including drug candidates, is achieved to illustrate the powerfulness of our method. A possible radical pathway is proposed according to the mechanism study.