Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling to Access Benzo[<i>c</i>]cinnolines
Shiyun Li, Yan An, Wei Zhao, Jun Huang, Bin Wen, Xingquan Chen
Abstract
In this paper, a highly efficient copper-catalyzed oxidative dehydrogenative coupling to obtain benzo[ c ]cinnolines (up to 100% yield) was developed. It was found that DMAP was a highly efficient ligand for copper-catalyzed oxidation, and molecular oxygen was a green oxidizing agent. In this simple process, various functional groups were tolerated under mild reaction conditions, and the practicality of the process was demonstrated by the preparation of benzo[ c ]cinnolines on a gram scale and later derivatization.
Topics & Concepts
ChemistryOxidative phosphorylationCatalysisCopperOxidative coupling of methaneCoupling (piping)Combinatorial chemistryMedicinal chemistryOrganic chemistryBiochemistryMetallurgyMaterials scienceCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAlkaloids: synthesis and pharmacology