TY - JOUR
T1 - Redox-Neutral P(O)-N Coupling between P(O)-H Compounds and Azides via Dual Copper and Photoredox Catalysis
AU - Wu, Yanan
AU - Chen, Ken
AU - Ge, Xia
AU - Ma, Panpan
AU - Xu, Zhiyuan
AU - Lu, Hongjian
AU - Li, Guigen
N1 - Publisher Copyright:
Copyright © 2020 American Chemical Society.
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2020/8/7
Y1 - 2020/8/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85088556768&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.0c02207
DO - 10.1021/acs.orglett.0c02207
M3 - Article
C2 - 32649207
AN - SCOPUS:85088556768
VL - 22
SP - 6143
EP - 6149
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 15
ER -