Title: Scalable Rh(III)‐Catalyzed Aryl C–H Phosphorylation Enabled by Anodic Oxidation‐Induced Reductive Elimination

Authors: Zheng-Jian Wu, Feng Su, Weidong Lin, Jinshuai Song, Ting-Bin Wen, Hui-Jun Zhang, Hai-Chao Xu

Abstract: 

Transition metal‐catalyzed C–H phosphorylation remains an unsolved challenge. Reported methods are generally limited in scope and require stoichiometric silver salts as oxidants. Herein we report an electrochemically driven Rh(III)‐catalyzed aryl C–H phosphorylation reaction, which proceeds through H2 evolution obviating the need for stoichiometric metal oxidants. The method is compatible with a variety of aryl C–H and P–H coupling partners and particularly useful for synthesizing triarylphosphine oxides from diarylphosphine oxides, which are often difficult coupling partners for transition metal‐catalyzed C–H phosphorylation reactions. Experimental results suggest that the mechanism responsible for the C–P bond formation involves an oxidation‐induced reductive elimination process.

Full-Link: https://onlinelibrary.wiley.com/doi/10.1002/anie.201909951