C–C Bond Cleavage at the N-α Position Enabled by the Low-potential Electrochemical Oxidation of the 2,7-Dimethoxynaphthyl Electroauxiliary

Abstract

Herein, we report that the 2,7-dimethoxynaphthyl (2,7-DMN) group is a novel electroauxiliary that is readily installed at the N-α position of a carbamate through Friedel–Crafts-type arylation. The resulting N-α C–C bond is easily cleaved through low-potential electrochemical oxidation to give the corresponding iminium cation.

Keywords

• electrosynthesis
• electroauxiliary
• radical cation
• iminium cation