Solvent-controlled nucleophilic trifluoromethylthiolation of Morita–Baylis–Hillman carbonates: dual roles of DABCO in activating the Zard's trifluoromethylthiolation reagent and the MBH carbonates

Abstract

A novel amine-catalyzed nucleophilic trifluoromethylthiolation between Morita–Baylis–Hillman carbonates and O-octadecyl-S-trifluorothiolcarbonate has been developed. The regioselectivity of this reaction can be controlled by choosing different solvents, affording primary allylic SCF₃ products in THF and secondary allylic SCF₃ products in CHCl₃ as major products. The mechanistic investigation indicated that DABCO plays a dual role in activating the Zard's trifluoromethylthiolation reagent and the MBH carbonates.