Concepedia

PhI(OCOCF<sub>3</sub>)<sub>2</sub>-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 Lü, Hong Wang, Chao Yang, Xiang Zhang, Daisy Zhang‐Negrerie, Yunfei Du, Kang Zhao

Organic Letters · 2013 · 76 citations · 57 references

DOI

Concepts

Abstract

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

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