Synthesis of α-Trifluoromethylthio-α,ß-Unsaturated Carbonyl Compounds by DABCO-Mediated Electrophilic Trifluoromethylthiolation with N-SCF3-Dibenzenesulfonimide.

ABSTRACT

A DABCO-mediated electrophilic α-trifluoromethylthiolation of α,ß-unsaturated carbonyl compounds comprising no ß-substituents has been achieved using N-trifluoromethylthio-dibenzenesulfonimide as the SCF3 source. The direct trifluoromethylthiolation provides the corresponding α-trifluoromethylthio-α,ß-unsaturated carbonyl products in good yields (up to 88%). Furthermore, the vinyl group in the α-trifluoromethylthio-α,ß-unsaturated carbonyl product was successfully transformed into diverse functional groups in good to excellent yields (70-95%) by reactions such as epoxidation, aziridination, hydrocyanation, and hydrogenation.