Redox-Neutral P(O)–N Coupling between P(O)–H Compounds and Azides via Dual Copper and Photoredox Catalysis
Yanan Wu, Ken Chen, Xia Ge, Panpan Ma, Zhiyuan Xu, Hongjian Lu, Guigen Li
Abstract
We report a redox-neutral P(O)-N coupling reaction of P(O)-H compounds with azides via photoredox and copper catalysis, providing new access to useful phosphinamides, phosphonamides, and phosphoramides. This transformation tolerates a wide range of nucleophilic functionalities including alcohol and amine nucleophiles, which makes up for the deficiency of classical nitrogen nucleophilic substitution reactions. As a demonstration of the broad potential applications of this new methodology, late-stage functionalization of a diverse array of azido-bearing natural products and drug molecules, a preliminary asymmetric reaction, and a continuous visible-light photoflow process have been developed.