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Ni-Catalyzed Reductive 1,2-Cross-Dialkylation of Unactivated Alkenes with Two Alkyl Bromides

Jianxin Zhang, Wei Shu

2022Organic Letters46 citationsDOI

Abstract

Cross-dialkylation of unactivated alkenes represents a significant challenge due to competitive β-hydride elimination and associated selectivity issues. Herein, a Ni-catalyzed reductive 1,2-dialkylation of unactivated aliphatic alkenes has been developed using two different alkyl bromides. The reaction proceeds smoothly under mild conditions to install two Csp3–Csp3 bonds onto directed aliphatic alkenes, demonstrating excellent chemo- and regioselectivity with good functional group tolerance.

Topics & Concepts

ChemistryAlkylCatalysisMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsFluorine in Organic Chemistry
Ni-Catalyzed Reductive 1,2-Cross-Dialkylation of Unactivated Alkenes with Two Alkyl Bromides | Litcius