Nickel-Catalyzed Enantioconvergent Ring-Opening Cross-Coupling of Aziridines with Arylboronic Acids

A nickel-catalyzed enantioconvergent ring-opening cross-coupling of racemic aziridines with arylboronic acids has been developed, affording a variety of enantioenriched 2,2-diarylethylamines under a redox-neutral manifold. This reaction proceeds under mild conditions without the need for stoichiometric reductants or photo- and electrochemical methods. Mechanistic studies suggest that the reaction proceeds via an iodide-mediated nucleophilic ring-opening of aziridines followed by stereoconvergent radical cross-coupling with the arylboronic acid. Furthermore, linear β-iodosulfonamides could undergo a 1,2-amino migration under the same catalytic conditions, yielding the same enantioenriched 2,2-diarylethylamine products with high efficiency. This divergent reactivity substantially broadens the utility and applicability of the methodology.