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Synfacts 2009(10): 1139-1139
DOI: 10.1055/s-0029-1217895
DOI: 10.1055/s-0029-1217895
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Functional Group Tolerant Kumada-Corriu-Tamao Coupling
Contributor(s):Paul Knochel, Tobias ThalerO. Vechorkin, V. Proust, X. Hu*
Ecole Polytechnique Fédérale de Lausanne, Switzerland
Functional Group Tolerant Kumada-Corriu-Tamao Coupling of Nonactivated Alkyl Halides with Aryl and Heteroaryl Nucleophiles: Catalysis by a Nickel Pincer Complex Permits the Coupling of Functionalized Grignard Reagents
J. Am. Chem. Soc. 2009, 131: 9756-9766
Ecole Polytechnique Fédérale de Lausanne, Switzerland
Functional Group Tolerant Kumada-Corriu-Tamao Coupling of Nonactivated Alkyl Halides with Aryl and Heteroaryl Nucleophiles: Catalysis by a Nickel Pincer Complex Permits the Coupling of Functionalized Grignard Reagents
J. Am. Chem. Soc. 2009, 131: 9756-9766
Further Information
Publication History
Publication Date:
22 September 2009 (online)
Key words
cross-coupling - Kumada-Corriu-Tamao coupling - Grignard reagents - nickel
Significance
The nickel(II) pincer complex 1 could be successfully used to promote a range of Kumada-Corriu-Tamao couplings using both functionalized organomagnesium reagents and alkyl iodides/bromides. Sensitive functional groups, such as ester, cyano, amide, and CF3 were well tolerated.
Comment
This Csp2 -Csp3 coupling reaction dis-plays a high generality, proceeds under mild reaction conditions, and leads to fast reaction times. These features make it a valuable tool for the coupling of aryl or heteroaryl organomagnesium reagents with non-activated β-hydride-containing primary and secondary alkyl halides.