Copper(I)-Catalyzed Three-Component Coupling of N-Tosylhydrazones, Alkynes and Azides: Synthesis of Trisubstituted 1,2,3-Triazoles

被引：64
|
作者：
Zhang, Zhikun [1 ,2 ]
Zhou, Qi [1 ,2 ]
Ye, Fei [1 ,2 ]
Xia, Ying [1 ,2 ]
Wu, Guojiao [1 ,2 ]
Hossain, Mohammad Lokman [1 ,2 ]
Zhang, Yan [1 ,2 ]
Wang, Jianbo [1 ,2 ,3 ]
机构：
[1] Peking Univ, Beijing Natl Lab Mol Sci BNLMS, Beijing 100871, Peoples R China
[2] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 10期
关键词：
carbenes; click reaction; copper; cross-coupling; multicomponent reaction; triazoles; COPPER-CATALYZED CYCLOADDITION; ONE-POT REACTION; MULTICOMPONENT REACTIONS; TERMINAL ALKYNES; REGIOSELECTIVE SYNTHESIS; ORGANIC AZIDES; COMPLEXITY; EFFICIENCY; CHEMISTRY; DESIGN;
D O I：
10.1002/adsc.201500377
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
The copper(I)-catalyzed three-component reaction of N-tosylhydrazones, terminal alkynes and azides has been realized in an efficient and regioselective manner. This reaction constitutes a convenient method for the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles from simple starting substrates. Mechanistically, the reaction involves the trapping of the copper(I) triazolide intermediate to form a copper carbene and subsequent migratory insertion and protonation.
引用
收藏
页码：2277 / 2286
页数：10
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