Pd-catalyzed double Heck and Heck–Suzuki cascade reaction of N-(o-bromo aryl) CF3-acrylamides

Abstract

A Pd-catalyzed double Heck and Heck–Suzuki cascade approach has been developed for the intramolecular cyclization of N-(o-bromoaryl)trifluoromethylacrylamide derivatives, followed by coupling with alkenes/phenyl boronic acids to produce trifluoromethyl-tethered 3,3-disubstituted oxindoles, without any external ligand. The resulting oxindoles feature an all-carbon quaternary center at the C3-position, accompanied by a CF₃ group that is believed to have potential for biological activity.