Nickel-catalyzed transamidation of aliphatic amide derivatives.

Nickel-catalyzed transamidation of aliphatic amide derivatives† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc01980g

Nickel-catalyzed coupling of isocyanates with 1,3-iodoesters and halobenzenes: a novel method for the synthesis of imide and amide derivatives.

Substituted imide and amide derivatives were conveniently prepared from the reaction of isocyanates with o-iodobenzoates and haloarenes catalyzed by the NiBr2(dppe)/dppe/Zn system in moderate to good yields with excellent tolerance of functional groups.

A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis

A long-standing challenge in synthetic chemistry is the development of the transamidation reaction. This process, which involves the conversion of one amide to another, is typically plagued by unfavourable kinetic and thermodynamic factors. Although some advances have been made with regard to the transamidation of primary amide substrates, secondary amide transamidation has remained elusive. He...

Discovery and mechanistic study of Al(III)-catalyzed transamidation of tertiary amides.

Cleavage of the C-N bond of carboxamides generally requires harsh conditions. This study reveals that tris(amido)Al(III) catalysts, such as Al2(NMe2)6, promote facile equilibrium-controlled transamidation of tertiary carboxamides with secondary amines. The mechanism of these reactions was investigated by kinetic, spectroscopic, and density functional theory (DFT) computational methods. The cata...

Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins.

Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (inclu...