Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls

An efficient electrochemical method for benzylic C(sp(3))-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O-2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, O-18 labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.

Automated summary

An efficient electrochemical method for benzylic C(sp(3))-H bond oxidation has been developed, which utilizes O-2 as the oxygen source and lutidinium perchlorate as an electrolyte in an undivided cell. The proposed single-electron transfer mechanism for the electrooxidation reaction was supported by cyclic voltammetry studies, O-18 labeling experiments, and radical trapping experiments.