3 years ago

A Consecutive C−H Functionalization Triggered by Oxidation of Active sp3 C−H Bonds: Construction of 3,4-Dihydroquinoline-3-one Derivatives

A Consecutive C−H Functionalization Triggered by Oxidation of Active sp3 C−H Bonds: Construction of 3,4-Dihydroquinoline-3-one Derivatives
Xiaodong Jia, Pengfei Li, Qian Chen, Yu Yuan, Honghe Ji, Xiaofei Liu, Wentao Hou, Yu Shao
We report a consecutive C−H functionalization that constructs 3,4-dihydroquinoline-3-one derivatives in high yields. This reaction is triggered by oxidation of active sp3 C−H bonds of glycines and N-benzylanilines. In this radical mediated transformation, four sp3 C−H bonds are functionalized efficiently, together with construction of one heterocyclic ring with a quaternary carbon center. A consecutive C−H functionalization was achieved by radical cation salt initiated aerobic oxidation, constructing 3,4-dihydroquinoline-3-one derivatives in high yields. In this consecutive process, oxidation of active sp3 C−H bonds of glycines and N-benzylanilines promoted further oxidation of inert C-H bonds, forging one heterocyclic ring with a quaternary carbon center.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702497

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