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Novel Synthesis of α-Keto Esters and Amides by an sp3 C-H Oxidation of Nitromethyl Aryl Ketones Promoted by Ion-Supported (Diacetoxyiodo)benzene

Xiaoying Jiang, Bing Gan, Jiwei Liu, Yuanyuan Xie*

*College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China, Email: xyyczzjut.edu.cn

X. Jang, B. Gan, J. Liu, Y. Xie, Synlett, 2016, 27, 2737-2741.

DOI: 10.1055/s-0035-1562535

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Abstract

In the presence of nucleophiles (alcohols or amines), ion-supported (di­acetoxyiodo)benzene promoted sp3 C-H oxidation of nitromethyl aryl ketones to provide the corresponding α-keto esters and amides in good yields. The reaction is ecofriendly and offers mild conditions, short reaction times, and a recyclable reagent.

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Key Words

keto esters, keto amides, hypervalent idione compounds, diacetoxyiodobenzene, nitromethyl aryl ketones, oxidation

ID: J60-Y2016