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Copper(I)‐Catalyzed Three‐Component Coupling of N ‐Tosylhydrazones, Alkynes and Azides: Synthesis of Trisubstituted 1,2,3‐Triazoles
Author(s) -
Zhang Zhikun,
Zhou Qi,
Ye Fei,
Xia Ying,
Wu Guojiao,
Hossain Mohammad Lokman,
Zhang Yan,
Wang Jianbo
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500377
Subject(s) - chemistry , regioselectivity , copper , protonation , catalysis , carbene , combinatorial chemistry , component (thermodynamics) , alkyne , organic chemistry , physics , thermodynamics , ion
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.