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Copper(I)‐Catalyzed Alkylation of Polyfluoroarenes through Direct CH Bond Functionalization
Author(s) -
Xu Shuai,
Wu Guojiao,
Ye Fei,
Wang Xi,
Li Huan,
Zhao Xia,
Zhang Yan,
Wang Jianbo
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201412450
Subject(s) - alkylation , surface modification , carbene , chemistry , diazo , copper , catalysis , combinatorial chemistry , fluorine , organic chemistry , polymer chemistry
The copper(I)‐catalyzed alkylation of electron‐deficient polyfluoroarenes with N‐tosylhydrazones and diazo compounds has been developed. This reaction uses readily available starting materials and is operationally simple, thus representing a practical method for the construction of C(sp 2 )C(sp 3 ) bonds with polyfluoroarenes through direct CH bond functionalization. Mechanistically, copper(I) carbene formation and subsequent migratory insertion are proposed as the key steps in the reaction pathway.