Nickel-Catalyzed Regioselective Cross-Dehydrogenative Coupling of Inactive C(sp3)-H Bonds with Indole Derivatives

A nickel-catalyzed regiosepecific C2- versus C3-oxidative cross-coupling reaction of indoles with 1,4-dioxane and other inactive C(sp(3))-H bonds is described. The divergent synthesis of C(sp(3))-C(sp(2)) bonds was achieved in satisfactory yields with di-tert-butyl peroxide (DTBP) as the oxidant, which provides an efficient strategy for the selective construction of cyclic ethers containing heteroaromatic core structures.