Palladium-Catalyzed Enantioselective C–H Arylations and Alkenylations of 2-Aminobiaryls with Atmospheric Air as the Sole Oxidant

Abstract

Optically active 2-aminobiaryls are valuable chiral frameworks with broad applications in catalysis, synthetic chemistry, and materials science. Here, we present a simple and practical methodology for their asymmetric synthesis via enantioselective palladium catalyzed C−H arylations or alkenylations of racemic precursors. The methodology utilizes a kinetic resolution strategy, producing two highly valuable enantioenriched axially chiral molecules: the C−C coupling product and the unreacted starting material. Notably, we have established reaction conditions that enable the in situ regeneration of the active Pd(II) catalyst using atmospheric air as the sole oxidant. Finally, we showcase the synthetic utility of this approach by preparing several derivatives relevant to the field of asymmetric catalysis.