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Paper | Special issue | Vol 52, No. 1, 2000, pp.303-312
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S25
A Convenient Synthesis of New 1-Alkynyl-1H-benzotriazoles by Reaction of Alkynyl(phenyl)iodonium Salts with Benzotriazole Ion

Tsugio Kitamura,* Norihiko Tashi, Kuniyuki Tsuda, Haiying Chen, and Yuzo Fujiwara*

*Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan


The reaction of arylethynyl(phenyl)iodonium tosylates with benzotriazole ion gave new 1-alkynyl-1H-benzotriazoles in good yields. This result indicates that alkynyliodonium salts can be used for direct alkynylation of benzotriazole. However, the similar reactions of (tert-butylethynyl)(phenyl)iodonium and 1-octynyl(phenyl)iodonium tosylates do not afford the 1-alkynyl-1H-benzotriazoles but alkenylbenzotriazoles via the reaction of alkylidenecarbenes.