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Nickel-Catalyzed Deaminative Acylation of Activated Aliphatic Amines with Aromatic Amides via C–N Bond Activation

Chu‐Guo Yu, Yutaka Matsuo

2020Organic Letters74 citationsDOIOpen Access PDF

Abstract

Deaminative functionalization of aliphatic primary amines has great synthetic utility. Herein, we describe a Ni-catalyzed reductive deaminative cross-electrophile coupling reaction between Katritzky salts and aromatic amides. This work provides examples of the synthesis of various ketones from alkylpyridinium salts, including both primary and secondary alkylamines. Given its mild reaction conditions and high functional group tolerance, this cross-coupling strategy is expected to be useful for late-stage functionalization of complex compounds.

Topics & Concepts

ChemistryAcylationCatalysisElectrophilePrimary (astronomy)Surface modificationOrganic chemistryCombinatorial chemistryFunctional groupAstronomyPhysicsPhysical chemistryPolymerAdvanced Synthetic Organic ChemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions
Nickel-Catalyzed Deaminative Acylation of Activated Aliphatic Amines with Aromatic Amides via C–N Bond Activation | Litcius