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Modular Access to Ketones via Cooperative NHC/Pd-Catalyzed C–H Alkylation of Aldehydes with Alkyl Bromides

Ying Huang, You-Feng Han, Chun-Lin Zhang, Song Ye

2023ACS Catalysis33 citationsDOI

Abstract

Direct C–H alkylation of aldehydes represents a straightforward and step-economy strategy for modular access to ketones. Herein, we report a direct C–H alkylation of aldehydes with alkyl bromides to generate ketones under cooperative NHC/Pd catalysis at room temperature. Secondary and the difficult-to-obtain tertiary alkyl-derived ketones could be prepared through this simple process under mild conditions. Mechanistic studies support the pathway involving generation of alkyl and ketyl radicals under NHC/Pd cooperative catalysis, and the following radical–radical coupling.

Topics & Concepts

AlkylationAlkylChemistryCatalysisKetylRadicalCombinatorial chemistryOrganic chemistryMedicinal chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions