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Copper‐Catalyzed Oxidative Dehydrogenative C(sp 3 )−H Bond Amination of (Cyclo)Alkanes using NH‐Heterocycles as Amine Sources
Author(s) -
Wang ChangSheng,
Wu XiaoFeng,
Dixneuf Pierre H.,
Soulé JeanFrançois
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201700783
Subject(s) - chemistry , amination , homolysis , bond cleavage , catalysis , medicinal chemistry , nitrile , oxidative coupling of methane , ketone , hydrogen peroxide , amine gas treating , copper , peroxide , organic chemistry , photochemistry , radical
A copper‐catalyzed oxidative C(sp 3 )−H/N−H coupling of NH‐heterocycles with affordable (cyclo)alkanes has been developed. This procedure involves C(sp 3 )−N bond formation through a radical pathway generated by homolytic cleavage of di‐ tert ‐butyl peroxide and trapping of the radical(s) by copper catalysts. The reaction tolerates a series of functional groups, such as bromo, fluoro, ester, ketone, nitrile, methyl, and methoxy. free‐NH‐containing indoles, pyrroles, pyrazoles, indazoles, and benzotriazoles are successfully N ‐alkylated.