Electrocatalytic Generation of Amidyl Radicals for Olefin Hydroamidation: Use of Solvent Effects to Enable Anilide Oxidation

Abstract

Oxidative generation of synthetically important amidyl radicals from N-H amides is an appealing and yet challenging task. Previous methods require a stoichiometric amount of a strong oxidant and/or a costly noble-metal catalyst. We report herein the first electrocatalytic method that employs ferrocene (Fc), a cheap organometallic reagent, as the redox catalyst to produce amidyl radicals from N-aryl amides. Based on this radical-generating method, an efficient intramolecular olefin hydroamidation reaction has been developed.

Keywords: amidyl radicals; electrochemistry; ferrocene; hydroamidation; redox catalysts.