Metal Cations from Sacrificial Anodes Act as a Lewis Acid Co-Catalyst in Electrochemical Cross-Coupling of Aryl Bromides and Aziridines

An efficient method for the reductive cross-electrophile coupling of aziridines with aryl halides using nickel electrocatalysis is reported. This reaction provides valuable phenethylamines at room temperature in good yields. The reaction was successfully applied to the electro-reductive cross-coupling of less reactive, unsubstituted N-tosylaziridine. Additionally, we were even able to couple challenging alkyl bromides with aryl aziridines. Control experiments and voltammetric studies confirm that the mechanism is distinct from conventional and photochemical couplings. Furthermore, the role of both Ni­(II) organometallic complexes and electrodes was examined, providing insight into the reaction mechanism and the beneficial role of the sacrificial anode in electrochemical cross-couplings.