Copper-Catalyzed Carbonylative Cross-Coupling of Alkyl Iodides and Amines.

Johanne Ling, Antoine Bruneau-Voisine, Guillaume Journot, Gwilherm Evano

Chemistry (Weinheim an der Bergstrasse, Germany) 2022 Aug 04

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A general copper-catalyzed carbonylative cross-coupling between amines and alkyl iodides is reported. Using a simple combination of catalytic amounts of copper(I) chloride and N,N,N',N",N"-pentamethyldiethylenetriamine in the presence of sodium hydroxide under carbon monoxide pressure, a broad range of alkyl iodides and amines can be efficiently coupled to the corresponding amides that are obtained in good to excellent yields. Notable features of this process - the first one relying on a base metal catalyst - include the availability and low cost of the catalytic system, its successful use with primary, secondary, tertiary alkyl iodides and all classes of amines - with no or limited competing nucleophilic substitution without CO incorporation - as well as its efficiency with complex alkyl iodides and amines. Mechanistic studies demonstrated that a radical pathway is operative and the key role of CO. © 2022 Wiley-VCH GmbH.

Citation

Johanne Ling, Antoine Bruneau-Voisine, Guillaume Journot, Gwilherm Evano. Copper-Catalyzed Carbonylative Cross-Coupling of Alkyl Iodides and Amines. Chemistry (Weinheim an der Bergstrasse, Germany). 2022 Aug 04;28(44):e202201356