ChemSusChem
ChemSusChem
5 years ago

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

Copper-Catalyzed Oxidative Dehydrogenative C(sp3)−H Bond Amination of (Cyclo)Alkanes using NH-Heterocycles as Amine Sources
Jean-François Soulé, Chang-Sheng Wang, Pierre H. Dixneuf, Xiao-Feng Wu
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. Outstanding achievement in amination: A variety of N-alkylated heterocycles is facilely synthesized by direct C−H bond amination of low-cost (cyclo)alkanes catalyzed by inexpensive copper salts. A wide range of NH-heterocycles are used as amine sources and the reaction displays good functional group compatibility.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/cssc.201700783

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