Trifluoromethylthio-promoted Nazarov cyclization of α-SCF3-vinyl (hetero)aryl ketones

Abstract

A trifluoromethylthio-promoted Nazarov cyclization of α-SCF₃-vinyl (hetero)aryl ketones has been developed using trifluoromethanesulfonic acid in dichloromethane. This efficient protocol affords the corresponding α-SCF₃-substituted cyclopentenone-fused polycyclic products in good yields (up to 96%). The bromo-substituted polycyclic products were further utilized in Sonogashira and Suzuki cross-coupling reactions, demonstrating their synthetic versatility. Density functional theory (DFT) calculations revealed that the α-SCF₃ substituent lowers the activation barrier, thereby facilitating the cyclization. This strategy provides an efficient route to a novel class of SCF₃-substituted polycyclic compounds.