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

Takizawa, K.; Nulwala, H.; Thibault, R.J.; Lowenhielm, P.; Yoshinaga, K.; Wooley, K.L.; Hawker, C.J.;
J. Polym. Sci., Polym. Chem.;
46, 2897-2912.

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.