Azides as an unconventional source of iminyl radicals: electrochemically induced synthesis of O-imido oximes from benzyl azides and N-hydroxyimides via N–O coupling

Abstract

Electrochemically induced synthesis of O-imido oximes from benzyl azides and N-hydroxyimides via N–O coupling has been discovered. The developed approach reveals a new role of benzyl azides in the practice of organic synthesis as precursors of iminyl radicals for intermolecular coupling reactions. The method is applicable to a wide range on benzyl azides and N-hydroxyimides, and O-imido oximes are obtained in yields up to 94%.