Trifluoromethylthiolation–arylation of diazocarbonyl compounds by modified Hooz multicomponent coupling

Abstract

A new Zn-mediated trifluoromethylthiolation-based bifunctionalization reaction is developed. In this process, simultaneous C–SCF₃ and C–C bond formation takes place in a multicomponent reaction, in which an aryl and a SCF₃ group arise from different reagents. Our studies show that the reaction mechanism is similar to the Hooz multicomponent coupling. The process involves in situ generation of BAr₃, which reacts with a diazocarbonyl compound, and the reaction is terminated by an electrophilic SCF₃ transfer. The reaction can also be extended to fluorination based bifunctionalization which proceeds with somewhat lower yield than the analogous trifluoromethylthiolation reaction.