Synthesis of macrocyclic heteroarylenes by consecutive inter- and intramolecular cycloadditions of thiophenylene-tethered triynes |
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| Authors: | Takanori Shibata Masako Fujimoto Takashi Otani |
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| Affiliation: | 1. Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo 169-8555, Japan;2. JST, ACT-C, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan;3. Research Center for Chirality, Research Institute for Science & Technology, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan |
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| Abstract: | ![]()
Consecutive inter- and intramolecular [2+2+2] cycloadditions of various thiophenylene-tethered triynes were comprehensively studied by using chiral Rh catalysts. When we started from 2,3- and 3,4-thiophenylene-tethered substrates, dimerization proceeded and chiral tetraheteroarylenes were obtained. In contrast, reactions of 2,5-thiophenylene-tethered substrates gave hexaheteroarylenes as trimers. When bis- and tris(2,5-thiophenylene)-tethered triynes were used, mixtures of dimers and trimers were obtained, which included macrocyclic systems that contained up to 12 aromatic rings, and their photophysical properties were measured. |
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| Keywords: | Cycloaddition Thiophene Chirality Heteroarylenes Asymmetric synthesis Macrocycles Rhodium |
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