Cu‐Catalyzed Oxidative Tandem Coupling and Cyclization of 2‐Aminonaphthalenes to Synthesize Dibenzo[c, g]carbazoles

Abstract

A Cu(II) complex with a bipyridyl ligand bearing a Brønsted acid was used to catalyze the tandem oxidative coupling and cyclization of 2‐aminonaphthalenes to give N‐substituted‐dibenzo[c,g]carbazoles. The incorporation of an appended acidic moiety to the ligand was found to be key to the selective formation of dibenzocarbazoles over 2,2’‐diamino‐1,1’‐binaphthalene (BINAM), which is known as an irreversible byproduct. This highly efficient method yields a wide array of dibenzo[c,g]carbazoles featuring diverse functional groups as well as electronic properties. The selected dibenzo[c,g]carbazoles exhibited high photoluminescence quantum yields of up to 100 % and are promising chromophores for advanced materials.