KINETIC STUDY ON HUISGEN REACTION CATALYZED BY COPPER(I): TRIAZOL FORMATION FROM WATER-SOLUBLE ALKYNE AND ALKYLAZIDE

被引：4
|
作者：
Kasuga, Yosuke [1 ]
Ito, Mamoru [1 ]
Onoda, Wataru [1 ]
Nakamura, Yosuke [1 ]
Inokuma, Seiichi [1 ]
Matsuda, Takehisa [2 ]
Nishimura, Jun [1 ]
机构：
[1] Gunma Univ, Grad Sch Engn, Dept Chem & Chem Biol, Gunma 3768515, Japan
[2] Kanazawa Inst Technol, Haku San, Ishikawa 9240838, Japan
来源：
HETEROCYCLES | 2009年 / 78卷 / 04期
关键词：
Click Chemistry; Huisgen Reaction; Triazole; Water-Soluble Azide; Second-Order Kinetics; CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITIONS; TERMINAL ALKYNES; AZIDES; LIGATION; PHASE;
D O I：
10.3987/COM-08-11592
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 degrees C.
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页码：983 / 997
页数：15
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