A Consecutive C−H Functionalization Triggered by Oxidation of Active sp3 C−H Bonds: Construction of 3, 4‐Dihydroquinoline‐3‐one Derivatives. Issue 53 (10th August 2017)

• Record Type: Journal Article
• Authors: Jia, Xiaodong; Hou, Wentao; Shao, Yu; Yuan, Yu; Chen, Qian; Li, Pengfei; Liu, Xiaofei; Ji, Honghe
• Is Part Of: Chemistry. Volume 23:Issue 53(2017)
• Page Start: 12980
• Page End: 12984
• Publication Date: 2017-08-10
• Subjects: 3, 4-dihydroquinoline-3-one -- aerobic oxidation -- C−H functionalization -- quaternary center -- radical cation; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201702497
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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 sp 3 C−H bonds of glycines and N ‐benzylanilines. In this radical mediated transformation, four sp 3 C−H bonds are functionalized efficiently, together with construction of one heterocyclic ring with a quaternary carbon center. Abstract : 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 sp 3 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.