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Synfacts 2010(8): 0888-0888  
DOI: 10.1055/s-0030-1257832
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Cyclyne via Mild Reductive Aromatization

Contributor(s): Timothy M. Swager, Stefanie A. Sydlik
K. Miki, M. Fujita, Y. Inoue, Y. Senda, T. Kowada, K. Ohe*
Kyoto University, Japan
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

A novel pyridine-containing cyclo­trimer was synthesized using a mild tin-mediated reductive aromatization as the key step in the formation of the completely conjugated, strained macrocycle. Direct cross-coupling of the para-phenyleneacetylene segments did not yield the desired macrocycle because of excessive ring strain. Attempting a sequential synthesis of the macrocycle 1 only improved the yield to 13%. The reductive aromatization of 1 to 2 was found to be very efficient (89% yield).