Electrochemical Deoxygenative Barbier-Type Reaction

An effective deoxygenative C(sp(3))-C(sp(3)) bond formation reaction is achieved through electrochemical reduction of alcoholic phosphates or sulfonates with aldehydes or ketones. Alcohol derivatives of phosphates undergo single-electron reduction under electrochemical conditions followed by a spontaneous cleavage of the C-O bond with the exothermic loss of phosphate resulting in an alkyl radical species. Subsequently, radical intermediates are further reduced to carbanions at the cathode, which are in situ trapped by carbonyl compounds, thus accomplishing a deoxygenative Barbier-type reaction.

Automated summary

In this study, an efficient deoxygenative C(sp(3))-C(sp(3)) bond formation reaction is achieved through the electrochemical reduction of alcoholic phosphates or sulfonates with aldehydes or ketones. The reaction proceeds under electrochemical conditions, where the alcohol derivatives of phosphates undergo single-electron reduction to generate alkyl radicals, which are further reduced at the cathode to carbanions and then react with carbonyl compounds.