Copper-Catalyzed Oxidative Dehydrogenative C(sp(3))-H Bond Amination of (Cyclo) Alkanes using NH-Heterocycles as Amine Sources

Chang-Sheng Wang (1) , Xiao-Feng Wu (2) , Pierre H. Dixneuf (1) , Jean-François Soulé (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LIKAT Rostock - Leibniz-Institut für Katalyse

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.

Keywords: alkanes; amination; c-h activation; copper; heterocycles

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Catalysis

Chang-Sheng Wang, Xiao-Feng Wu, Pierre H. Dixneuf, Jean-François Soulé. Copper-Catalyzed Oxidative Dehydrogenative C(sp(3))-H Bond Amination of (Cyclo) Alkanes using NH-Heterocycles as Amine Sources. ChemSusChem, 2017, 10 (15), pp.3075-3082. ⟨10.1002/cssc.201700783⟩. ⟨hal-01578538⟩