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Synfacts 2006(6): 0571-0571  
DOI: 10.1055/s-2006-934510
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

A One-Pot Synthesis and Functionalization of Polyynes

Contributor(s): Timothy M. Swager, Mark S. Taylor
Y. Morisaki, T. Luu, R. R. Tykwinski*
University of Alberta, Edmonton, Canada
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

The preparation of lithiated derivatives of butadiyne and hexatriyne, and the coupling reactions of these species, are described. Dibromoolefin precursors are converted by Fritsch-Buttenburg-Wiechell (FBW, see review) rearrangement into lithium acetylides in the presence of n-butyllithium. These species are employed, without further purification, in carbon-carbon bond-forming reactions with aldehydes, ketones, carbon dioxide, epoxides, and iodo­methane, as well as Negishi and Stille cross-couplings.