Cobalt-Catalyzed Cross-Dehydrogenative Coupling Reaction between Unactivated C(sp²)–H and C(sp³)–H Bonds

Catalytic oxidative cross-dehydrogenative coupling between unactivated C­(sp²)–H and C­(sp³)–H bonds is achieved by the cobalt-catalyzed o-alkylation reaction of aromatic carboxamides containing (pyridin-2-yl)­isopropyl amine (PIP–NH₂) as a N,N-bidentate directing group. Many different C­(sp³)–H bonds in alkanes, toluene derivatives and even in the α-position of ethers and thioethers can be used as coupling partners. This method has a broad substrate scope and the tolerance of various functional groups.