Electroreductive Cross-Electrophile Coupling of Aziridines and Aryl Bromides

Chemistry. 2023 Jun 27;29(36):e202300959. doi: 10.1002/chem.202300959. Epub 2023 May 5.

Abstract

Herein, a nickela-electrocatalyzed cross-electrophile coupling of readily available aryl aziridines and aryl bromides under mild and sustainable electrochemical conditions to access synthetic useful β-arylethylamines is developed. This protocol is characterized by its exquisite chemo- and regioselectivity, broad substrate scope and good functional group compatibility. Mechanistic studies confirmed that the regioselectivity and reactivity observed are a result of electro-induced ring-opening of aziridines under electroreductive conditions to generate a benzyl radical intermediate as the active species. Furthermore, this strategy also enables cross-coupling with CO2 to access β-amino acids under mild conditions.

Keywords: aryl bromides; aziridines; cross-coupling; electrochemistry; electroreduction.