PhI(OCOCF₃)₂-Mediated C-C Bond Formation Concomitant with a 1,2-Aryl Shift in a Metal-Free Synthesis of 3-Arylquinolin-2-ones

Le Liu, Hang Lu, Hong Wang, Chao Yang, Xiang Zhang, Daisy Zhang-Negrerie, Yunfei Du* and Kang Zhao*

*Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China, Email: duyunfeiertju.edu.cn, kangzhaotju.edu.cn

L. Liu, H. Lu, H. Wang, C. Yang, X. Zhang, D. Zhang-Negrerie, Y. Du, K. Zhao, Org. Lett., 2013, 15, 2903-2909.

DOI: 10.1021/ol400743r

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Abstract

A general and efficient reaction of readily available N-methyl-N-phenylcinnamamides with phenyliodine bis(trifluoroacetate) (PIFA) in the presence of Lewis acids provides various 3-arylquinolin-2-one compounds in good yields. This novel approach features not only metal-free oxidative C(sp²)-C(sp²) bond formation but also an exclusive 1,2-aryl migration.

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Key Words

2-Quinolones, PIFA

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ID: J54-Y2013