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Synfacts 2009(6): 0614-0614  
DOI: 10.1055/s-0029-1216660
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Catenanes from Intramolecular Diyne Coupling

Contributor(s): Timothy M. Swager, Jason R. Cox
Y. Sato, R. Yamasaki, S. Saito*
Tokyo University of Science, Japan
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

This work explores the formation of [2]catenanes through intramolecular oxidative diyne coupling promoted by copper(I) complexes. The authors examined the influence of the structure of the alkyne and the resulting yields to determine optimal conditions for threading and coupling. The yields varied from trace amounts to 64% in the best scenario. The authors also propose a mechanism to account for the various side products such as intermolecular coupling and intramolecular cyclization.