The　incorporation　of　trifluoromethylthio　group　(-SCF3)　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.　©　2022　The　Authors.　Published　by　American　Chemical　Society.