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Synfacts 2006(7): 0711-0711  
DOI: 10.1055/s-2006-941880
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Cu-Catalyzed Preparation of 1,4-Diynes from TMS Alkynes

Contributor(s): Paul Knochel, Andrei Gavryushin
F. Montel, R. Beaudegnies, J. Kessabi, B. Martin, E. Muller, S. Wendeborn, P. M. J. Jung*
Syngenta Crop Protection AG, Basel, Switzerland
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Publikationsdatum:
22. Juni 2006 (online)

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Significance

1,4-Diynes are direct precursors of a very important class of natural compounds: polyunsaturated fatty acids. Herein, the authors described a new procedure, allowing the preparation of polyfunctionalized 1,4-diynes from readily available materials: TMS alkynes and propargylic chlorides, using a catalytic amount of copper. This method overcomes the existing procedures in terms of chemoselectivity and tolerance to functional groups, as no strong bases are present in the reaction mixture.