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Metal-Free Tandem Oxidative Aryl Migration and C-C Bond Cleavage: Synthesis of α-Ketoamides and Esters from Acrylic Derivatives

Le Liu, Liang Du, Daisy Zhang-Negrerie, Yunfei Du* and Kang Zhao*

*School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China, Email:,

L. Liu, L. Du, D. Zhang-Negrerie, Y. Du, K. Zhao, Org. Lett., 2014, 16, 5772-5775.

DOI: 10.1021/ol502834g


A tandem metal-free oxidative aryl migration/C-C bond-cleavage reaction, mediated by hypervalent iodine reagent, provides straightforward access to important α-ketoamide and α-ketoester derivatives from readily available acrylic derivatives via a concerted process of 1,2-aryl shift concomitant with C-C bond cleavage.

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Key Words

acylations, PIDA

ID: J54-Y2014