Copper-Catalyzed Asymmetric Arylation of N-Heteroaryl Aldimines: Elementary Step of a 1,4-Insertion

Abstract

Copper complexes of monodentate phosphoramidites efficiently promote asymmetric arylation of N-azaaryl aldimines with arylboroxines. DFT calculations and experiments support an elementary step of 1,4-insertion in the reaction pathway, a step in which an aryl-copper species adds directly across four atoms of C=N-C=N in the N-azaaryl aldimines.

Keywords: 1,4-insertion; arylation; asymmetric catalysis; copper catalysis; phosphoramidate.