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Synthesis 2010(9): 1500-1504  
DOI: 10.1055/s-0029-1218688
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Mediated Homocoupling of Vinyl Dibromides to Symmetrical Diynes

Alexis Coste, François Couty, Gwilherm Evano*
Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint Quentin en Yvelines, 45 avenue des Etats-Unis, 78035 Versailles Cedex, France
Fax: +33(1)39254452; e-Mail: evano@chimie.uvsq.fr;
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Publication History

Received 7 December 2009
Publication Date:
24 February 2010 (online)

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Abstract

1,1-Dibromoalk-1-enes were dimerized readily in the presence of copper iodide, a diamine ligand, and cesium carbonate in DMF to give symmetrical 1,3-diynes. The reaction was found to be selective and rather general, furnishing the corresponding diynes in good yields, even with complex and sensitive dibromides, and provides useful insights into the reactivity of 1,1-dibromoalk-1-enes with copper(I).

Key words

dibromoalkenes - copper catalysis - 1,3-diynes

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