Aerobic Oxidative Synthesis of N‐Containing Heterocycles from o‐Substituted Aniline Derivatives and Primary Amines by Perylene Diimide Catalysis

The commercially available 3,4,9,10‐perylenetetracarboxylic diimide (PTCDI) acted as a heterogeneous catalyst to catalyze aerobic oxidative synthesis of benzimidazoles, benzothiazoles, and quinoxalines from o‐substituted aniline derivatives and primary amines in high yields with oxygen as the terminal oxidant. The gram scale reaction and reusability (up to six cycles) of the PTCDI catalyst were also successful and would greatly benefit industrial applications. Oxidative cyclization of o‐substituted aniline derivatives with primary amines for the synthesis of benzimidazoles, benzothiazoles, and quinoxalines with oxygen as the terminal oxidant, the method used the commercially available organocatalyst PTCDI as a heterogeneous catalyst and can be recycled six times without significant loss of catalytic activity.