Publication

Cross Coupling of Non-Activated Alkyl Halides by a Nickel Pincer Complex

2010
Journal Articles

Abstract

Non-activated alkyl halides are challenging substrates for cross-coupling reactions because they are reluctant to undergo oxidative addition and because metal alkyl intermediates are prone to β-H elimination. Despite recent progress, well-defined catalysts are rare. We recently prepared Ni complexes with a chelating pincer-type bis(amino)amide ligand. The chloride complex [(MeNN2)NiCl] is an active (pre)catalyst for the coupling of non-activated alkyl halides with alkyl, aryl, and heteroaryl Grignard reagents. The catalysis tolerates a wide range of functional groups such as keto, ester, amide, acetal, indole, furan, nitrile, etc. The Ni complex also catalyzes direct alkylation of alkynes and aromatic heterocycles.

Official source

https://infoscience.epfl.ch/entities/publication/b39c92a9-4a68-4b4e-98f9-6399b5ad7b7c

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2010
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/b39c92a9-4a68-4b4e-98f9-6399b5ad7b7c

About this result

Related concepts (32)

Kumada coupling

In organic chemistry, the Kumada coupling is a type of cross coupling reaction, useful for generating carbon–carbon bonds by the reaction of a Grignard reagent and an organic halide. The procedure uses transition metal catalysts, typically nickel or palladium, to couple a combination of two alkyl, aryl or vinyl groups. The groups of Robert Corriu and Makoto Kumada reported the reaction independently in 1972. The reaction is notable for being among the first reported catalytic cross-coupling methods.

Cross-coupling reaction

In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important reaction type is this: (R, R' = organic fragments, usually aryle; M = main group center such as Li or MgX; X = halide) These reactions are used to form carbon–carbon bonds but also carbon-heteroatom bonds. Cross-coupling reaction are a subset of coupling reactions.

Coupling reaction

In organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (where R = organic group, M = main group centre metal atom) reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. Richard F.

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Cross Coupling of Non-Activated Alkyl Halides by a Nickel Pincer Complex

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