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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
Further Information

Publication History

Publication Date:
20 November 2009 (online)

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Ni-Catalyzed Sonogashira Coupling of Nonactivated Alkyl HalidesSynfacts 2010; 2010(01): 0127-0127
DOI: 10.1055/s-0029-1219039

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.