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-electrophilecouplingof aziridines with aryl halides using nickel electrocatalysis is reported.This reaction provides valuable phenethylamines at room temperaturein good yields. The reaction was successfully applied to the electro-reductivecross-coupling of less reactive, unsubstituted N-tosylaziridine.Additionally, we were even able to couple challenging alkyl bromideswith aryl aziridines. Control experiments and voltammetric studiesconfirm that the mechanism is distinct from conventional and photochemicalcouplings. Furthermore, the role of both Ni(II) organometallic complexesand electrodes was examined, providing insight into the reaction mechanismand the beneficial role of the sacrificial anode in electrochemicalcross-couplings.

Automated summary

An efficient method for the reductive cross-electrophile coupling of aziridines with aryl halides using nickel electrocatalysis is reported. Valuable phenethylamines are synthesized at room temperature in good yields. The reaction is distinct from conventional and photochemical couplings, and the role of Ni(II) organometallic complexes and electrodes in the reaction mechanism are examined.