Nickel-Catalyzed Enantioselective Electrochemical Reductive Cross-Coupling of Aryl Aziridines with Alkenyl Bromides

An electrochemically driven nickel-catalyzed enantioselective reductive cross-coupling of aryl aziridines with alkenyl bromides has been developed, affording enantioenriched beta-aryl homoallylic amines with excellent E-selectivity. This electroreductive strategy proceeds in the absence of heterogeneous metal reductants and sacrificial anodes by employing constant current electrolysis in an undivided cell with triethylamine as a terminal reductant. The reaction features mild conditions, remarkable stereocontrol, broad substrate scope, and excellent functional group compatibility, which was illustrated by the late-stage functionalization of bioactive molecules. Mechanistic studies indicate that this transformation conforms with a stereoconvergent mechanism in which the aziridine is activated through a nucleophilic halide ring-opening process.

Automated summary

An electrochemically driven nickel-catalyzed enantioselective reductive cross-coupling reaction was developed for the synthesis of enantioenriched beta-aryl homoallylic amines with excellent E-selectivity. This reaction proceeds under mild conditions without the use of heterogeneous metal reductants and sacrificial anodes, employing constant current electrolysis with triethylamine as a terminal reductant. The reaction demonstrates remarkable stereocontrol, broad substrate scope, and excellent functional group compatibility, making it suitable for the late-stage modification of bioactive molecules.