Copper-catalyzed versatile C(sp3)-H arylation: synthetic scope and regioselectivity investigations

The copper-catalyzed versatile C(sp2)-C(sp3) bond formation with N-heteroaromatics and hydrogen donors was developed. Various alkanes and ethers reacted with quinolines, isoquinolins, pyridines, benzooxazole and benzothiazole to give the corresponding C(sp2)-H alkylation products via cross-dehydrogenative coupling. On the other hand, we achieved the high regioselective C(sp2)-halogen alkylation of (hetero) aryl chlorides and (hetero) aryl bromides with ethers via elimination of the halogen radical. The reaction mechanism was investigated with control experiments.