Title: Synthesis of [2]Catenanes by Oxidative Intramolecular Diyne Coupling Mediated by Macrocyclic Copper(I) Complexes
Abstract: Angewandte Chemie International EditionVolume 48, Issue 3 p. 504-507 Communication Synthesis of [2]Catenanes by Oxidative Intramolecular Diyne Coupling Mediated by Macrocyclic Copper(I) Complexes† Correction(s) for this article Synthesis of [2]Catenanes by Oxidative Intramolecular Diyne Coupling Mediated by Macrocyclic Copper(I) Complexes Yuta Sato, Ryu Yamasaki Dr., Shinichi Saito Dr., Volume 48Issue 15Angewandte Chemie International Edition pages: 2630-2630 First Published online: March 24, 2009 Yuta Sato, Yuta Sato Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorRyu Yamasaki Dr., Ryu Yamasaki Dr. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorShinichi Saito Dr., Shinichi Saito Dr. [email protected] Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this author Yuta Sato, Yuta Sato Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorRyu Yamasaki Dr., Ryu Yamasaki Dr. Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this authorShinichi Saito Dr., Shinichi Saito Dr. [email protected] Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601 (Japan) http://www.rs.kagu.tus.ac.jp/sslab/Search for more papers by this author First published: 29 December 2008 https://doi.org/10.1002/anie.200804864Citations: 86 † We thank the Yamada Science Foundation and the UBE Foundation for the financial support of this work. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Right said thread: Oxidative intramolecular coupling reactions of α,ω-diynes in the presence of macrocyclic phenanthroline CuI complexes allows the synthesis of [2]catenanes in up to 64 % yield (see scheme). The bond-forming reaction leads to concurrent threading of the diyne through the phenanthroline macrocycle. Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description anie_200804864_sm_miscellaneous_information.pdf4.6 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 1aV. Serreli, C. F. Lee, E. R. Key, D. A. Leigh, Nature 2007, 445, 523–527; 1bV. Balzani, A. Credi, B. Ferrer, S. Silvi, M. Venturi, Top. Curr. Chem. 2005, 262, 1–27; 1cC. P. Mandl, B. König, Angew. Chem. 2004, 116, 1650–1652; Angew. Chem. Int. Ed. 2004, 43, 1622–1624; 1dJ. V. Hernandez, E. R. Key, D. A. Leigh, Science 2004, 306, 1532–1537. 2 2aS. Bonnet, J. P. Collin, M. Koizumi, P. Mobian, J. P. Sauvage, Adv. Mater. 2006, 18, 1239–1250; 2bJ. E. Green, J. W. Choi, A. Boukai, Y. Bunimovich, E. Johonston-Halperin, E. Delonno, Y. Luo, B. A. Sheri ff, K. Xu, Y. S. Shin, H. R. Tseng, J. F. Stoddart, J. R. Health, Nature 2007, 445, 414–417; 2cA. H. Flood, J. F. Stoddart, J. R. Health, Science 2004, 306, 2055–2056; 2d Molecular Switches (Eds.: ), Wiley-VCH, Weinheim, 2001. 3E. J. Wasserman, J. Am. Chem. Soc. 1960, 82, 4433–4434. 4 4aG. Schill, C. Zürcher, Angew. Chem. 1969, 81, 996–997; Angew. Chem. Int. Ed. Engl. 1969, 8, 988–988; 4bG. Schill, E. Logemam, W. Vetter, Angew. Chem. 1972, 84, 1144–1145; Angew. Chem. Int. Ed. Engl. 1972, 11, 1089–1090; 4cFor review, see, G. Schill in Catenanes, Rotaxanes, and Knots (Eds: ), Academic Press, New York, 1971. 5 5aC. O. Dietrich-Buchecker, J. P. Sauvage, J. P. Kintzinger, Tetrahedron Lett. 1983, 24, 5095–5098; 5bC. O. Dietrich-Buchecker, J. P. Sauvage, Chem. Rev. 1987, 87, 795–810. 6aF. M. Raymo, J. F. Stoddart, Chem. Rev. 1999, 99, 1643–1663; 6bT. Ikeda, S. Saha, I. Aprahamian, K. C. F. Leung, A. Williams, W. Q. Deng, A. H. Flood, W. A. Goddart, J. F. Stoddart, Chem. Asian J. 2007, 2, 76–93; 6cM. Fujita, F. Ibukuro, H. Hagihara, K. Ogura, Nature 1994, 367, 720–723. 7aC. A. Schalley, W. Reckien, S. Peyerimhoff, B. Baytekin, F. Vögtle, Chem. Eur. J. 2004, 10, 4777–4789; 7bF. Vögtle, S. Meier, R. Hoss, Angew. Chem. 1992, 104, 1628–1631; Angew. Chem. Int. Ed. Engl. 1992, 31, 1619; 7cA. M. L. Fuller, D. A. Leigh, P. J. Lusby, A. M. Z. Slawin, D. B. Walker, J. Am. Chem. Soc. 2005, 127, 12612–12619. 8J. Berná, J. D. Crowley, S. M. Goldup, K. D. Hänni, A. L. Lee, D. A. Leigh, Angew. Chem. 2007, 119, 5811–5815; Angew. Chem. Int. Ed. 2007, 46, 5709–5713. 9S. Saito, E. Takahashi, K. Nakazono, Org. Lett. 2006, 8, 5133–5136. 10V. Aucagne, K. D. Hänni, D. A. Leigh, P. J. Lusby, D. B. Walker, J. Am. Chem. Soc. 2006, 128, 2186–2187. 11V. Aucagne, J. Berná, J. D. Crowely, S. M. Goldup, K. D. Hänni, D. A. Leigh, P. J. Lusby, V. E. Ronaldson, A. M. Z. Slawin, A. Viterisi, D. B. Walker, J. Am. Chem. Soc. 2007, 129, 11950–11963. 12See the Supporting Information. 13At the same time, we examined the cyclization of 2 in the presence of an acyclic phenanthroline Cu complex. No correlation was evident between the yield of the cyclized product and the yield of the catenane. 14T. C. Higgs, S. Parsons, P. J. Bailey, A. C. Jones, F. McLachlan, A. Parkin, A. Dawson, P. A. Tasker, Organometallics 2002, 21, 5692–5702. 15The precise structure of the intermediate of this reaction is not clear, and CuI/CuIII interconversion could be another possibility. The final important intermediate, however, should be a monomeric dialkynyl Cu species. The dimeric Cu complex which is postulated in some reactions would not form as an intermediate for this reaction. See, 15aJ. Berná, S. M. Goldup, A. L. Lee, D. A. Leigh, M. D. Symes, G. Teobaldi, F. Zerbetto, Angew. Chem. 2008, 120, 4464–4468; Angew. Chem. Int. Ed. 2008, 47, 4392–4396; 15bW. Y. Lo, C.-H. Lam, V. W. W. Yam, N. Zhu, K. K. Cheung, S. Fathallaf, S. Messaoudi, B. L. Guennic, S. Kahlal, J. F. Halet, J. Am. Chem. Soc. 2004, 126, 7300–7310; 15cP. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. 2000, 112, 2740–2767; Angew. Chem. Int. Ed. 2000, 39, 2632–2657. 16The macrocyclic Cu complexes used in this study are efficient catalysts for the oxidative coupling of small alkynes such as 4-methoxyphenylacetylene and the coupling product was isolated in more than 90 % yield in the presence of a catalytic amount (10 mol %) of the complex. Therefore, in principle, the reaction of a molecule of 1 would proceed with more than two molecules of the diyne, and a multicatenane could be isolated. However, we could not isolate a multicatenane from the reaction mixture. The study directed toward the formation of the multicatenane is ongoing. Citing Literature Volume48, Issue3January 5, 2009Pages 504-507 ReferencesRelatedInformation