Generation and Reaction of Benzyl Triflates by Anodic Oxidation of Toluenes

Abstract

Direct functionalization of benzylic C–H bonds provides an attractive route to access valuable benzylic derivatives, but selective oxidation remains challenging due to overoxidation of the desired products. Herein, we report a new electrochemical strategy for the generation and utilization of benzyl triflates. In this study, benzyl triflates were successfully generated from two-electron oxidation of toluenes, and their formation was directly confirmed by NMR spectroscopy. The anodically generated triflates were subsequently converted into benzylic ethers and thioethers. This approach suppresses overoxidation by generating cationic intermediates under nucleophile-free conditions, which can then be selectively transformed.