Alkynylation of Benzotriazole with Silylethynyliodonium Triflates. Regioselective Synthesis of 2-Ethynyl-2H-benzotriazole Derivatives

作者：Kitamura Tsugio^*; Morshed Mohammad Hasan; Tsukada Satoru; Miyazaki Yuki; Iguchi Naomi; Inoue Daisuke

来源：Journal of Organic Chemistry, 2011, 76(19): 8117-8120.

DOI：10.1021/jo2015467

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 (BuOH)-Bu-t and CH2Cl2 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.

• 出版日期2011-10-7