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Publication

Nickel-catalyzed diastereoselective alkyl-alkyl Kumada coupling

Xile Hu, Peng Ren, Thomas Clément Di Franco, Pablo Marcelo Perez Garcia
2012
Journal Articles

Abstract

A nickel pincer complex is found to catalyze alkyl–alkyl Kumada coupling reactions of 1,3- and 1,4-substituted cyclohexyl halides and tetrahydropyrans with an excellent diastereoselectivity. The mechanistic investigation of the coupling reactions provides evidence that the activation of alkyl halides is reversible.

Official source

https://infoscience.epfl.ch/entities/publication/2f61ee1e-88e1-4832-985c-8fd32f2652ab

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Xile Hu, Peng Ren, Thomas Clément Di Franco, Pablo Marcelo Perez Garcia
2012
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/2f61ee1e-88e1-4832-985c-8fd32f2652ab

About this result

Related concepts (8)

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.

Suzuki reaction

The Suzuki reaction is an organic reaction, classified as a cross-coupling reaction, where the coupling partners are a boronic acid and an organohalide and the catalyst is a palladium(0) complex. It was first published in 1979 by Akira Suzuki, and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichi Negishi for their contribution to the discovery and development of palladium-catalyzed cross-couplings in organic synthesis. This reaction is also known as the Suzuki–Miyaura reaction or simply as the Suzuki coupling.

Hiyama coupling

The Hiyama coupling is a palladium-catalyzed cross-coupling reaction of organosilanes with organic halides used in organic chemistry to form carbon–carbon bonds (C-C bonds). This reaction was discovered in 1988 by Tamejiro Hiyama and Yasuo Hatanaka as a method to form carbon-carbon bonds synthetically with chemo- and regioselectivity. The Hiyama coupling has been applied to the synthesis of various natural products.

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Nickel-catalyzed diastereoselective alkyl-alkyl Kumada coupling

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