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Copper‐Catalyzed Arylation of Remote C(sp 3 )−H Bonds in Carboxamides and Sulfonamides
Author(s) -
Li Zhaodong,
Wang Qian,
Zhu Jieping
Publication year - 2018
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.201807623
Subject(s) - chemistry , copper , catalysis , carbon atom , medicinal chemistry , hydrogen bond , carbon fibers , hydrogen atom , combinatorial chemistry , molecule , organic chemistry , ring (chemistry) , group (periodic table) , materials science , composite number , composite material
Reported herein is an unprecedented copper‐catalyzed arylation of remote C(sp 3 )−H bonds. Stirring a trifluorotoluene solution of either N‐fluorocarboxamides or N‐fluorosulfonamides and arylboronic acids in the presence of a catalytic amount of copper(II) trifluoroacetylacetonate, 2,2′‐bipyridine, and sodium tert ‐butoxide afforded the γ‐ and δ‐C(sp 3 )−H arylated carboxamides and sulfonamides, respectively, in good to high yields. Mechanistic studies indicate that the reaction might proceed through an amidyl radical generation, 1,5‐hydrogen atom transfer (HAT), and copper‐catalyzed cross‐coupling of the resulting carbon radical with arylboronic acids.