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Paper | Regular issue | Vol 78, No. 4, 2009, pp.983-997
Published online, 22nd December, 2008
DOI: 10.3987/COM-08-11592
Kinetic Study on Huisgen Reaction Catalyzed by Copper(I): Triazol Formation from Water-Soluble Alkyne and Alkyl Azide

Yosuke Kasuga, Mamoru Ito, Wataru Onoda, Yosuke Nakamura, Seiichi Inokuma, Takehisa Matsuda, and Jun Nishimura*

*Department of Chemistry, Gunma University, 1-5-1 Tenjin-cho, Kiryu 376-8515, Japan

Abstract

The kinetics was examined for the copper(I)-catalyzed Huisgen reaction. Despite the complex reaction pathway, it was successfully analyzed by the second-order kinetics with equal amounts of two organic substrates in the presence of 0.1 equivalent of copper catalyst, after dividing the time course into two stages, the early and late ones. Both stages gave almost the same activation parameters. The reaction of water-soluble alkyl azide (1) was 60 times as fast as that of water-soluble aromatic azide (4) at the early stage and surprisingly 822 times after 15 min reaction time at 30 ˚C.