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Synfacts 2006(8): 0783-0783  
DOI: 10.1055/s-2006-941962
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Indeno-Fused Aromatics by [2+2+2] Cycloaddition

Contributor(s): Timothy M. Swager, Mark S. Taylor
Y.-T. Wu, T. Hayama, K. K. Baldridge, A. Linden, J. S. Siegel*
University of Zürich, Switzerland and National Cheng-Kung University, Tainan, Taiwan
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Publication History

Publication Date:
21 July 2006 (online)

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Significance

The rhodium-catalyzed [2+2+2] cycloaddition of diynes and alkynes is employed as the key step in an efficient and modular synthesis of fluoranthenes and indenocorannulenes. The success of the rhodium-catalyzed cycloaddition for the construction of such sterically crowded products is worthy of note (see review below for a discussion of metal-catalyzed [2+2+2] reactions). This protocol is compatible with substrates bearing useful functional groups, including esters, alcohols, and aryl halides. The ability to carry out high-yielding formal [2+2+2] reactions of acetylene using norbornadiene as an acetylene equivalent is of considerable interest from the standpoint of ease of operation and safety.