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Nickel-Catalyzed Amination of Alkyl Electrophiles

Qing Wang, Xiangzhang Tao, Shengyang Ni, Yi Pan, Yi Wang

2023Organic Letters10 citationsDOI

Abstract

Bimolecular nucleophilic substitution S N 2 is the earliest and most important means of amination of alkyl electrophiles; its practical utilization is largely limited to primary or activated substrates. Furthermore, a persistent challenge lies in establishing C(sp 3 )–N bonds from alkyl substrates in cross-coupling chemistry using palladium and nickel catalysts. Therefore, the methods of constructing C(sp 3 )–N bonds remain rare from alkyl electrophiles. The existing routes are limited to copper catalysis and photoredox catalysis. Here, we demonstrate an alternative amination strategy for rapid construction of C(sp 3 )–N bonds from accessible alkyl electrophiles, which were used as radical precursors under nickel catalysis by Ni (III) species reductive eliminations in high efficiency.

Topics & Concepts

ChemistryAminationElectrophileAlkylNucleophileCatalysisElectrophilic aminationNickelPalladiumCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions
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