Ni/Photoredox-Catalyzed C(sp³)-C(sp³) Coupling between Aziridines and Acetals as Alcohol-Derived Alkyl Radical Precursors.

ABSTRACT: Aziridines are readily available C(sp³) precursors that afford valuable β-functionalized amines upon ring opening. In this article, we report a Ni/photoredox methodology for C(sp³)-C(sp³) cross-coupling between aziridines and methyl/1°/2° aliphatic alcohols activated as benzaldehyde dialkyl acetals. Orthogonal activation modes of each alkyl coupling partner facilitate cross-selectivity in the C(sp³)-C(sp³) bond-forming reaction: the benzaldehyde dialkyl acetal is activated via hydrogen atom abstraction and β-scission via a bromine radical (generated in situ from single-electron oxidation of bromide), whereas the aziridine is activated at the Ni center via reduction. We demonstrate that an Ni(II) azametallacycle, conventionally proposed

SUBMITTER: Dongbang S 

PROVIDER: S-EPMC10281197 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature