Facile syntheses of 4-vinyl-1,2,3-triazole monomers by click azide/acetylene coupling

Authors

  • Kenichi Takizawa,

    1. Department of Chemistry and Biochemistry, Materials Research Laboratory, University of California, Santa Barbara, California 93106
    2. Mitsubishi Chemical Group Science and Technology Research Center, Inc., 1000 Kamoshida-Cho, Aoba-Ku, Yokohama 227-8502, Japan
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  • Hunaid Nulwala,

    1. Department of Chemistry and Biochemistry, Materials Research Laboratory, University of California, Santa Barbara, California 93106
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  • Raymond J. Thibault,

    1. Department of Chemistry and Biochemistry, Materials Research Laboratory, University of California, Santa Barbara, California 93106
    2. The Dow Chemical Company, B1608 Freeport, Texas 77598
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  • Peter Lowenhielm,

    1. Department of Chemistry and Biochemistry, Materials Research Laboratory, University of California, Santa Barbara, California 93106
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  • Kohji Yoshinaga,

    1. Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology, Tobata, Kitakyushu, Fukuoka 804-8550, Japan
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  • Karen L. Wooley,

    1. Department of Chemistry, Washington University in St. Louis, St. Louis, Missouri 63130
    2. Department of Radiology, Washington University in St. Louis, St. Louis, Missouri 63110
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  • Craig J. Hawker

    Corresponding author
    1. Department of Chemistry and Biochemistry, Materials Research Laboratory, University of California, Santa Barbara, California 93106
    • Department of Chemistry and Biochemistry, Materials Research Laboratory, University of California, Santa Barbara, California 93106
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Abstract

Synthetic strategies for the preparation of a new family of vinyl monomers, 4-vinyl-1,2,3-triazoles, have been developed. These monomers are noteworthy as they combine the stability and aromaticity of styrenics with the polarity of vinylpyridines and the structural versatility of acrylate/methacrylate derivatives. To enable the wide adoption of these unique monomers, new methodologies for their synthesis have been elaborated which rely on Cu-catalyzed azide/acetylene cycloaddition reactions—“click chemistry”—as the key step, with the vinyl substituent being formed by either elimination or Wittig-type reactions. In addition, one-pot “click” reactions have been developed from alkyl halides, which allow for monomer synthesis without isolation of the intermediate organic azides. The high yield and facile nature of these procedures has allowed a library of new monomers including the parent compound, 1-H-4-vinyl-1,2,3-triazole, to be prepared on large scales. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 2897–2912, 2008

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