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Cu(I)‐Catalyzed Three‐Component Coupling of Trifluoromethyl Ketone N ‐Tosylhydrazones, Alkynes and Azides: Synthesis of Difluoromethylene Substituted 1,2,3‐Triazoles
Author(s) -
Zhang Zhikun,
Zhou Qi,
Yu Weizhi,
Li Tianjiao,
Zhang Yan,
Wang Jianbo
Publication year - 2017
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600888
Subject(s) - chemistry , trifluoromethyl , ketone , catalysis , substrate (aquarium) , carbene , combinatorial chemistry , component (thermodynamics) , coupling (piping) , coupling reaction , fluoride , organic chemistry , medicinal chemistry , inorganic chemistry , mechanical engineering , oceanography , alkyl , physics , engineering , thermodynamics , geology
A CuI ‐catalyzed three‐component coupling of trifluoromethyl ketone N ‐ tosylhydrazones, alkynes and azides has been developed . The reactionrepresents a straightforward method to access difluoromethylene substituted 1,2,3‐triazoles. Mechanistically, it has been proposed that the reaction follows a pathway involving the formation of Cu(I)triazolide intermediate, Cu(I) carbene formation, migratory insertion, and β ‐fluoride elimination. Thetransformation is featured by mild conditions, wide substrate scope and high efficiency.