Direct copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with AgSCF3

Abstract

A copper-catalyzed direct oxidative trifluoromethylthiolation of aryl boronic acids with AgSCF₃ has been developed. This approach provides straightforward and efficient access to a variety of aryl trifluoromethyl sulfides from an easily prepared and stable nucleophilic trifluoromethylthiolation reagent AgSCF₃, and readily available nucleophilic aryl boronic acids, thus avoiding the preparation of electrophilic trifluoromethylthiolating reagents in advance. Preliminary mechanistic experiments indicated that AgSCF₃ served as both a source of SCF₃ and an oxidant.