Visible-Light-Induced Photocatalysis of 1,1,1-Trifluoro-2-iodoethane with Alkylalkenes and Silyl Enol Ethers

Reactions of 1,1,1-trifluoro-2-iodoethane with alkylalkenes and silyl enol ethers were performed in the presence of a catalytic amount of fac-Ir(ppy)(3) and an excessive amount of Hunig's base in acetonitrile irradiated by a 24 W fluorescent lamp under nitrogen atmosphere for 48 hours. The visible-light-induced photoredox reactions introduce simultaneously a 2,2,2-trifluoroethyl group and an iodine atom to both sides of the double bond of ordinary alkenes via an atom-transfer radical addition (ATRA). The same reaction with silyl enol ethers generates -trifluoromethyl ketones, which are typically a challenge to synthesize. The reactions proved to be tolerant of a variety of functionalities.