Ni-Catalyzed Addition of Arylborons to Alkenes for the Synthesis of Quaternary Carbon Centers

Abstract All-carbon quaternary centers are prevalent structural motifs, thus attracting increasing interest from the organic community. We present here a nickel-catalyzed, Markovnikov-selective addition of stable organoborons to simple alkenes, enabled by a diimine ligand. This robust method provides efficient access to quaternary carbon centers with high yields. Furthermore, with a bulky chiral diimine ligand, quaternary carbon stereocenters can be readily prepared. Mechanistic investigations indicate the involvement of an unusual nickel migration from an alkyl nickel to an aryl nickel species.