Deoxytrifluoromethylthiolation and Selenylation of Alcohols by Using Benzothiazolium Reagents

Aliphatic compounds substituted with medicinally important trifluoromethylthio (SCF₃) and trifluoromethylselenyl (SeCF₃) groups were synthesized directly from alcohols by using the new benzothiazolium salts BT-SCF₃ and BT-SeCF₃ . These bench-stable fluorine-containing reagents are facile to use and can be prepared in two steps from non-fluorinated heteroaromatic starting materials. The metal-free deoxytrifluoromethylthiolation process using BT-SCF₃ proceeds under mild conditions and the similarly efficient trifluoromethylselenylation reactions using BT-SeCF₃ are, to the best of our knowledge, the first reported examples of this transformation.