Copper-Catalyzed Oxidative Dehydrogenative C(sp3)−H Bond Amination of (Cyclo)Alkanes using NH-Heterocycles as Amine Sources

Chang Sheng Wang; Xiao Feng Wu; Pierre H. Dixneuf; Jean François Soulé

doi:10.1002/cssc.201700783

Copper-Catalyzed Oxidative Dehydrogenative C(sp³)−H Bond Amination of (Cyclo)Alkanes using NH-Heterocycles as Amine Sources

Chang Sheng Wang, Xiao Feng Wu, Pierre H. Dixneuf, Jean François Soulé

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

A copper-catalyzed oxidative C(sp³)−H/N−H coupling of NH-heterocycles with affordable (cyclo)alkanes has been developed. This procedure involves C(sp³)−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.

Original language	English
Pages (from-to)	3075-3082
Number of pages	8
Journal	ChemSusChem
Volume	10
Issue number	15
DOIs	https://doi.org/10.1002/cssc.201700783
State	Published - 10 Aug 2017
Externally published	Yes

Keywords

C−H activation
alkanes
amination
copper
heterocycles

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10.1002/cssc.201700783

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abstract = "A copper-catalyzed oxidative C(sp3)−H/N−H coupling of NH-heterocycles with affordable (cyclo)alkanes has been developed. This procedure involves C(sp3)−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.",

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doi = "10.1002/cssc.201700783",

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AU - Wu, Xiao Feng

AU - Dixneuf, Pierre H.

AU - Soulé, Jean François

PY - 2017/8/10

Y1 - 2017/8/10

N2 - A copper-catalyzed oxidative C(sp3)−H/N−H coupling of NH-heterocycles with affordable (cyclo)alkanes has been developed. This procedure involves C(sp3)−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.

AB - A copper-catalyzed oxidative C(sp3)−H/N−H coupling of NH-heterocycles with affordable (cyclo)alkanes has been developed. This procedure involves C(sp3)−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.

KW - C−H activation

KW - alkanes

KW - amination

KW - copper

KW - heterocycles

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DO - 10.1002/cssc.201700783

M3 - 文章

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AN - SCOPUS:85022323889

SN - 1864-5631

VL - 10

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ER -

Copper-Catalyzed Oxidative Dehydrogenative C(sp³)−H Bond Amination of (Cyclo)Alkanes using NH-Heterocycles as Amine Sources

Abstract

Keywords

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