Electrochemical Oxidation of Benzyl Alcohols via Hydrogen Atom Transfer Mediated by 2,2,2-Trifluoroethanol
Takahiro Kawajiri1, Masahiro Hosoya1, Satoshi Goda1
1API R&D Laboratory, Research Division, Shionogi & Co., Ltd., 1-3, Kuise Terajima 2-Chome, Amagasaki, Hyogo 660-0813, Japan.
Abstract:
We report a novel electrochemical oxidation of benzyl alcohols. We found that trifluoroethanol plays a role as a hydrogen atom transfer (HAT) mediator, enabling the oxidation of electron-deficient substrates that are difficult to directly oxidize on electrode surfaces. Density functional theory calculations, cyclic voltammetry measurements, and constant potential electrolysis studies supported the proposed HAT mechanism. Moreover, the obtained carbonyl compounds could be functionalized in an electrochemical one-pot manner, further highlighting their synthetic utility.
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