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

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)6143-6149
Number of pages7
JournalOrganic Letters
Volume22
Issue number15
DOIs
StatePublished - Aug 7 2020

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