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

页码：2277 / 2286

页数：10

共 84 条

[81] CuBr-Catalyzed Coupling of N-Tosylhydrazones and Terminal Alkynes: Synthesis of Benzofurans and Indoles [J].