Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF3-containing five-membered cyclic carbonates†

Abstract

A visible-light-induced photocatalytic oxytrifluoromethylation reaction of alkenes has been reported for the efficient synthesis of diverse five-membered cyclic carbonates and vicinal diols bearing trifluoroethyl substituted quaternary centers under mild conditions. This protocol features a broad substrate scope and the ability to be performed on a gram scale. Mechanistic studies indicate that the reaction undergoes a process of oxidative radical-polar crossover, leading to the formation of a benzylic carbocation which then undergoes nucleophilic cyclization.