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

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.