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

Authors

  • Prof. Dr. Munetaka Kunishima,

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    1. Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan)
    2. 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)
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  • Kanako Kikuchi,

    1. Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)
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  • Yukio Kawai,

    1. Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)
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  • Dr. Kazuhito Hioki

    1. Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)
    2. Cooperative Research Center of Life Sciences, Kobe Gakuin University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586 (Japan)
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  • This work was supported partially by a Grant-in-Aid for Scientific Research (No. 20390007) from Japan Society for the Promotion of Science (JSPS).

Abstract

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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.

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