Enantioselective Pd-catalyzed dearomative reductive Heck and domino Heck–Suzuki reactions of 2-CF3-indoles

Abstract

Highly enantioselective palladium-catalyzed dearomative reductive Heck reaction and domino Heck–Suzuki reaction of 2-CF₃-indoles have been developed. Using Pd(OAc)₂/(R)-Synphos as the catalyst and Et₃SiH as a hydride source, a variety of indolines bearing a 2-trifluoromethyl quaternary stereocenter were obtained via a dearomative reductive Heck reaction. Alternatively, using Pd(dba)₂/phosphoramidite as the catalyst and Ar₄BNa as a coupling partner, structurally diverse indolines containing two vicinal carbon stereocenters were afforded through the domino dearomative Heck–Suzuki reaction.