An Electroreductive Approach to Nickel-Catalyzed Enantioselective Cross-Coupling of Aryl Aziridines

Key words

aryl aziridines - electrochemistry - homoallylic amines - nickel catalysis - reductive cross-coupling - vinyl bromides

Significance

Nevado and co-workers report an electroreductive strategy for the stereoconvergent nickel-catalyzed cross-electrophile coupling of aryl aziridines with vinyl bromides. This method features excellent functional group tolerance and remarkable stereocontrol, providing access to a broad range of highly enantioenriched β-aryl homoallylic amines.

Comment

Mechanistic investigations, including radical trapping experiments with TEMPO and cyclic voltammetry studies, support the shown catalytic cycle. The stereoconvergent nature of this process relies on the intermediate formation of β-halo amines through nucleophilic halide ring opening.

Publication History

Article published online:
11 May 2023