A Novel Electrophilic-Type Trifluoromethylthiolation Reagent, Shibata Reagent II

Shibata et al. have reported a novel trifluoromethylthiolating reaction using an electrophilic-type trifluoromethylthiolation reagent, benzoyl(phenyliodonio)(trifluoromethanesulfonyl)methanide (Shibata Reagent II). This reagent is electrophilic and reacts well with various nucleophiles to afford the CF₃S-substituted products. The reaction process is assumed that a reactive trifluoromethylthio (CF₃S−) species is generated from the trifluoromethanesulfonyl group by carbene-mediated in situ reduction catalyzed by a copper (I) salt in the presence of an amine. Trifluoromethylthiolated compounds have attracted special interest in the pharmaceutical and agrochemical industries.