Trifluoromethylthiolation–arylation of diazocarbonyl compounds by modified Hooz multicomponent coupling

A new Zn-mediated trifluoromethylthiolation-based bifunctionalization reaction is developed. In this process, simultaneous C–SCF(3) and C–C bond formation takes place in a multicomponent reaction, in which an aryl and a SCF(3) 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 BAr(3), which reacts with a diazocarbonyl compound, and the reaction is terminated by an electrophilic SCF(3) transfer. The reaction can also be extended to fluorination based bifunctionalization which proceeds with somewhat lower yield than the analogous trifluoromethylthiolation reaction.