Deoxytrifluoromethylthiolation and Selenylation of Alcohols by Using Benzothiazolium Reagents.

Aliphatic compounds substituted with medicinally important trifluoromethylthio (SCF ) and trifluoromethylselenyl (SeCF ) groups were synthesized directly from alcohols by using the new benzothiazolium salts BT-SCF and BT-SeCF . 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-SCF proceeds under mild conditions and the similarly efficient trifluoromethylselenylation reactions using BT-SeCF are, to the best of our knowledge, the first reported examples of this transformation.