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Synfacts 2009(12): 1383-1383  
DOI: 10.1055/s-0029-1218170
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Ni-Catalyzed Sonogashira Coupling of Nonactivated Alkyl Halides

Contributor(s):Paul Knochel, Andrei Gavryushin
O. Vechorkin, D. Barmaz, V. Proust
Ecole Polytechnique Fédérale de Lausanne, Switzerland
Ni-Catalyzed Sonogashira Coupling of Nonactivated Alkyl Halides: Orthogonal Functionalization of Alkyl Iodides, Bromides, and Chlorides
J. Am. Chem. Soc.  2009,  131:  12078-12079  
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Publication History

Publication Date:
20 November 2009 (online)

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Key words

Sonogashira coupling - terminal alkynes - alkylation - alkyl halides - nickel

Significance

The Sonogashira cross-coupling of nonactivated, β-H-containing alkyl halides is a highly challenging reaction. Use of nickel(II) pincer complex 1, developed by the authors, allows for a simple and versatile coupling of functionalized alkyl halides, including chlorides, with various terminal alkynes. This is an excellent method for the preparation of internal alkynes.

Comment

The nickel(II) pincer complex 1 is also a versatile catalyst for the Kumada sp³-sp² coupling (O. Vechorkin, V. Proust, X. L. Hu J. Am. Chem. Soc. 2009, 131, 9756). Contrary to the classical Sonogashira coupling, aryl halides are not reactive under these conditions. This method is more convenient than the classical alkyne alkylation, which requires harsh basic conditions.

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