The incorporation of trifluoromethylthio group (−SCF 3 ) into small molecules has attracted considerable attention recently, because of its unique properties, which are beneficial for drug discovery. The preparation of trifluoromethylthiolated (hetero)arenes, a leading class of trifluoromethylthiolated compounds, is one of the hot topics in organic chemistry frontiers, and much effort have been exerted to access them. In this review, special attention is given to the preparation of (hetero)aryl C−H bonds by Friedel−Crafts-type trifluoromethylthiolation and transition-metal-catalyzed aromatic C− H bond activation/trifluoromethylthiolation with electrophilic trifluoromethylthiolating reagents.