A convergent paired electrolysis strategy enables the cross-coupling of methylarenes with imines

Abstract

In this report, we have developed a metal-free convergent paired electrolysis strategy for α-benzyl amine synthesis from readily available imines and methylarenes, taking advantage of both anodic oxidation and cathodic reduction. This thiol-mediated convergent paired electrolysis protocol fulfils critical and multifaceted roles, not only activating benzylic C–H bonds at the anode to access benzylic radicals, but also reducing imines to α-aminoalkyl radical species at the cathode, which facilitates radical–radical cross-coupling, avoiding the use of metals or stoichiometric oxidants. Key to the success of this electrolysis is to match the two desirable half reactions simultaneously, in which a benzylic radical and an α-aminoalkyl radical species interact with each other, giving rise to the desired α-benzyl amine products.