Synergistic palladium/copper-catalyzed Csp3–Csp2 cross-couplings using aldehydes as latent α-alkoxyalkyl anion equivalents

Abstract

The first Csp³–Csp² cross-coupling using aldehydes as latent α-alkoxyalkyl anion equivalents has been achieved. The synergistic palladium/copper-catalyzed reaction of aromatic aldehydes and aryl bromides with a silylboronate afforded the three-component coupling products, silyl-protected benzhydrol derivatives. The reaction pathway involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(I) species followed by its palladium-catalyzed cross-coupling with aryl bromides.