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Synfacts 2007(4): 0381-0381  
DOI: 10.1055/s-2007-968312
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Silafluorene Synthesis

Contributor(s): Timothy M. Swager, Eric L. Dane
T. Matsuda, S. Kadowaki, T. Goya, M. Murakami*
Kyoto University, Japan
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Publication History

Publication Date:
23 March 2007 (online)

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Significance

An iridium-catalyzed [2+2+2] cyclo­addition of silicon-bridged diynes leads to the formation of silafluorene derivatives. Although requiring elevated temperatures, the reaction proceeds without the strongly basic and/or reducing conditions that have previously been used to synthesize silafluorenes. The authors report that the reaction also occurs with rhodium catalysis, but in lower yields. Unsubstituted terminal alkynes lead to a significantly lower yield in the one example presented by the authors.