Electrochemical Desaturative β-Acylation of Cyclic N-Aryl Amines

Herein, we disclose a straightforward, robust, and simple route to access beta-substituted desaturated cyclic amines via an electrochemically driven desaturative beta-functionalization of cyclic amines. This transformation is based on multiple single-electron oxidation processes using catalytic amounts of ferrocene. The reaction proceeds in the absence of stoichiometric amounts of electrolyte under mild conditions, affording the desired products with high chemo- and regioselectivity. The reaction was tolerant of a broad range of substrates and also enables late-stage beta-C(sp(3))-H acylation of potentially valuable products. Preliminary mechanistic studies using cyclic voltammetry reveal the key role of ferrocene as a redox mediator in the reaction.

Automated summary

This study presents a new method for the preparation of beta-substituted desaturated cyclic amines through electrochemical desaturative beta-functionalization, which is simple, robust, and exhibits good substrate tolerance.