Electrochemical Oxidation-Induced Oxyphosphorylation of Alkenes and Alkynes with Water via Hydrogen Atom Transfer

A metal- and exogenous-oxidant-free oxidation-induced oxyphosphorylation of alkenes and alkynes with water for beta-ketophosphonates has been developed through the radical coupling under electrochemical conditions. This protocol is compatible with a wide range of alkenes, alkynes, and diarylphosphorus derivatives, and enables the gramscale synthesis of beta-ketophosphonates. The mechanistic study revealed that the P radicals were generated via hydrogen atom transfer (HAT) event jointly mediated by tetrabutylammonium acetate and anode oxidation process.

Automated summary

A metal- and exogenous-oxidant-free oxidation-induced oxyphosphorylation method for the synthesis of beta-ketophosphonates from alkenes and alkynes using water has been developed under electrochemical conditions. The protocol is compatible with a wide range of substrates and allows for gramscale synthesis of the desired products.