Substrate‐Selective Dehydrocondensation at the Interface of Micelles and Emulsions of Common Surfactants

Angewandte Chemie International EditionVolume 51, Issue 9 p. 2080-2083 Communication Substrate-Selective Dehydrocondensation at the Interface of Micelles and Emulsions of Common Surfactants† Prof. Dr. Munetaka Kunishima, Corresponding Author Prof. Dr. Munetaka Kunishima [email protected] Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan) Cooperative Research Center of Life Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan)Search for more papers by this authorKanako Kikuchi, Kanako Kikuchi Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)Search for more papers by this authorYukio Kawai, Yukio Kawai Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)Search for more papers by this authorDr. Kazuhito Hioki, Dr. Kazuhito Hioki Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan) Cooperative Research Center of Life Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)Search for more papers by this author Prof. Dr. Munetaka Kunishima, Corresponding Author Prof. Dr. Munetaka Kunishima [email protected] Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan) Cooperative Research Center of Life Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan)Search for more papers by this authorKanako Kikuchi, Kanako Kikuchi Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)Search for more papers by this authorYukio Kawai, Yukio Kawai Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)Search for more papers by this authorDr. Kazuhito Hioki, Dr. Kazuhito Hioki Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan) Cooperative Research Center of Life Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)Search for more papers by this author First published: 20 January 2012 https://doi.org/10.1002/anie.201107706Citations: 30 † This work was supported partially by a Grant-in-Aid for Scientific Research (No. 20390007) from Japan Society for the Promotion of Science (JSPS). 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 Scratch the surface: Dehydrocondensations between carboxylates and amines by using an amphiphilic 1,3,5-triazinylammonium-based coupling agent were accelerated by the interfacial effect of micelles and emulsions of common surfactants (see figure). The reaction of carboxylates was promoted by both anionic and nonionic surfactants, and that of amines was promoted by only a nonionic surfactant. High selectivities for more lipophilic substrates were observed in micelles or emulsions. 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_201107706_sm_miscellaneous_information.pdf282.2 KB 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 1J. H. Fendler, E. J. Fendler, Catalysis in Micellar and Macromolecular Systems, Academic Press, New York, 1975. 2J. H. Fendler, Membrane Mimetic Chemistry, Wiley, New York, 1982. 3S. Tascioglu, Tetrahedron 1996, 52, 11113–11152. 4T. Dwars, E. Paetzold, G. Oehme, Angew. Chem. 2005, 117, 7338–7364; Angew. Chem. Int. 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