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Nickel‐Catalyzed Selective Synthesis of α‐Alkylated Ketones via Dehydrogenative Cross‐Coupling of Primary and Secondary Alcohols

Amreen K. Bains, Ayanangshu Biswas, Debashis Adhikari

2021Advanced Synthesis & Catalysis37 citationsDOI

Abstract

Abstract Herein, we describe an isolable, air‐stable, homogeneous, nickel catalyst that performs dehydrogenative cross‐coupling reaction between secondary and primary alcohols to result α‐alkylated ketone products selectively. The sequence of steps involve in this one‐pot reaction is dehydrogenation of both alcohols, condensation between the ketone and the aldehyde, and hydrogenation of the in situ‐generated α,β‐unsaturated ketone. Preliminary mechanistic investigation hints a radical mechanism following borrowing hydrogen reaction. magnified image

Topics & Concepts

ChemistryDehydrogenationKetoneAlkylationAldehydeCatalysisPrimary (astronomy)Organic chemistryNickelCoupling reactionHomogeneous catalysisCombinatorial chemistryAstronomyPhysicsAsymmetric Hydrogenation and CatalysisCarbon dioxide utilization in catalysisCatalytic C–H Functionalization Methods