title: Alkynylation of benzotriazole with silylethynyliodonium triflates. Regioselective synthesis of 2-ethynyl-2H-benzotriazole derivatives.
abstract: Phenyl(trimethylsilylethynyl)iodonium and tert-butyldimethylsilylethynyl(phenyl)iodonium triflates were applied to alkynylation of benzotriazole. Treatment of the silylethynyliodonium triflates with the potassium salt of benzotriazole ion in (t)BuOH and CH(2)Cl(2) gave 2-(trimethylsilylethynyl)-2H-1,2,3-benzotriazole and 2-(tert-butyldimethylsilylethynyl)-2H-1,2,3-benzotriazole in 74% and 76% yields, respectively. The regioisomers, 1-silylethynyl-1H-1,2,3-benzotriazole derivatives, were minor. In both cases of the silyl-substitued ethynyliodonium salts, novel regioselective alkynylation of benzotriazole at the 2 position was observed.
authors.affiliation: Department of Chemistry and Applied Chemistry, Graduate School of Science and Engineering, Saga University, Honjo-machi, Saga 840-8502, Japan. kitamura@cc.saga-u.ac.jp
authors.forename: Tsugio
authors.initials: T
authors.lastname: Kitamura
authors.forename: Mohammad Hasan
authors.initials: MH
authors.lastname: Morshed
authors.forename: Satoru
authors.initials: S
authors.lastname: Tsukada
authors.forename: Yuki
authors.initials: Y
authors.lastname: Miyazaki
authors.forename: Naomi
authors.initials: N
authors.lastname: Iguchi
authors.forename: Daisuke
authors.initials: D
authors.lastname: Inoue