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Synfacts 2009(6): 0672-0672  
DOI: 10.1055/s-0029-1216777
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Metal-Free Sonogashira Coupling

Contributor(s): Benjamin List, Kristina Zumbansen
R. Luque, D. J. Macquarrie
University of York, UK and Universidad de Córdoba, Spain
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

Luque and Macquarrie report a metal-free Sonogashira coupling using a range of substituted aryl iodides in a solvent- and phosphane-free protocol. Several basic molecules were tested as catalysts, but only 1,4-diazabi­cyclo(2.2.2)octane (DABCO) gave reasonable conversions. Conventional heating provides the cross-coupling products with high conversion and selectivities. Microwave irradiation reduced the ­reaction times (1-2 h) and improved the selectivities further (>95%).