title: Modular synthesis of bis- and tris-1,2,3-triazoles by permutable sequential azide-aryne and azide-alkyne cycloadditions.
abstract: A modular synthetic method for bis- and tris-1,2,3-triazoles that include a benzotriazole structure was developed on the basis of sequential azide-aryne and azide-alkyne cycloadditions. The key to success was efficient halogen-metal exchange reaction-mediated generation of aryne from ortho-iodoaryl triflates bearing a base-sensitive terminal alkyne moiety, which was achieved using trimethylsilylmethyl Grignard reagent.
authors.affiliation: Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan. thosoya.cb@tmd.ac.jp.
authors.forename: Suguru
authors.initials: S
authors.lastname: Yoshida
authors.forename: Takako
authors.initials: T
authors.lastname: Nonaka
authors.forename: Takamoto
authors.initials: T
authors.lastname: Morita
authors.forename: Takamitsu
authors.initials: T
authors.lastname: Hosoya
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry*; D061565:Cycloaddition Reaction; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000480:Alkynes; D001386:Azides; D014230:Triazoles; D001554:Benzene