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β-二酮和β-酮酯与羧酸的电化学诱导分子间交叉脱氢C-O偶联反应

Electrochemically Induced Intermolecular Cross-Dehydrogenative C-O Coupling of β-Diketones and β-Ketoesters with Carboxylic Acids.

作者信息

Bityukov Oleg V, Matveeva Olesya K, Vil' Vera A, Kokorekin Vladimir A, Nikishin Gennady I, Terent'ev Alexander O

机构信息

N. D. Zelinsky Institute of Organic Chemistry , Russian Academy of Sciences , 47 Leninsky prosp. , Moscow 119991 , Russian Federation.

D. I. Mendeleev University of Chemical Technology of Russia , 9 Miusskaya Square , Moscow 125047 , Russian Federation.

出版信息

J Org Chem. 2019 Feb 1;84(3):1448-1460. doi: 10.1021/acs.joc.8b02791. Epub 2019 Jan 23.

Abstract

The electrochemically induced cross-dehydrogenative C-O coupling of β-diketones and β-ketoesters (C-H reagents) with carboxylic acids (O-H reagents) was developed. An important feature of this reaction lies in the selective formation of intermolecular C-O coupling products in high yields, up to 92%, using DMSO as a solvent with a broad substrate scope in an undivided cell equipped with carbon and platinum electrodes at high current density. Electric current acts as a stoichiometric oxidant.

摘要

开发了β-二酮和β-酮酯(C-H试剂)与羧酸(O-H试剂)的电化学诱导交叉脱氢C-O偶联反应。该反应的一个重要特点是,在配备碳电极和铂电极的未分隔电解池中,以DMSO为溶剂,在高电流密度下,能以高达92%的高产率选择性地形成分子间C-O偶联产物,底物范围广泛。电流充当化学计量氧化剂。

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