Deoxytrifluoromethylthiolation and Selenylation of Alcohols by Using Benzothiazolium Reagents

Chemistry. 2019 Jun 7;25(32):7635-7639. doi: 10.1002/chem.201901607. Epub 2019 May 13.

Abstract

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.

Keywords: alcohols; fluorine; reagent development; trifluoromethylselenyl group; trifluoromethylthio group.