Naphthylpyridyl-Cu(II)-Catalyzed Oxidative Coupling of 2-Naphthylamines to Access BINAM Derivatives

Abstract

In this study, we report the efficient synthesis of 1,1 '-binaphthyl-2,2 '-diamine (BINAM) derivatives via copper-catalyzed oxidative coupling of 2-aminonaphthalenes. The use of a ligand featuring an extended pi system in combination with Cu(II) and molecular oxygen as the terminal oxidant enabled the formation of various BINAM derivatives in yields of up to 84%. Mechanistic investigations suggest a redox pathway involving Cu(II)/Cu(I) cycling, and pi-pi interactions between the ligand and substrate are proposed to stabilize reactive intermediates, thereby contributing to the observed efficiency.