Visible light driven C–N cross-coupling reactions catalysed by a conjugated polymer network

Abstract

This work describes the use of a fluorine and triazine containing conjugated polymer network (CPN) susceptible to in situ Pd doping during its preparation for photocatalytic C–N cross-coupling reactions between aryl halides and amines under visible light irradiation at room temperature. Comprehensive mechanistic investigations were conducted in order to understand the role of each variable and reactive species involved in the reaction pathway. The broad substrate range (aliphatic, aromatic, and heterocyclic) with good functional group tolerance, recyclability, low catalyst loading (5.0 wt%), use of low intensity white LED light (0.05 W cm⁻²), high yields (95–82%), and high turnover frequency values of up to 1515.46 h⁻¹ are some of the primary advantages of the described method. The CPN photocatalyzed gram-scale synthesis of high-value compounds like 4-(4-nitrophenyl)morpholine, 4-phenylmorpholone, and N-benzylpyridine-2-amine further illustrated the practical utility of the proposed approach.