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铜催化氧化偶联实现的α,β-不饱和酸的脱羧烷基羧化反应

Decarboxylative Alkylcarboxylation of α,β-Unsaturated Acids Enabled by Copper-Catalyzed Oxidative Coupling.

作者信息

Gao Bao, Xie Yinjun, Shen Zhiqiang, Yang Lei, Huang Hanmin

机构信息

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences , Lanzhou 730000, P. R. China.

出版信息

Org Lett. 2015 Oct 16;17(20):4968-71. doi: 10.1021/acs.orglett.5b02382. Epub 2015 Sep 29.

Abstract

A facile and general method for copper-catalyzed decarboxylative alkylcarboxylation of cinnamic acids with dimethyl 2,2'-azobis(2-methylpropionate) has been developed. The scope and versatility of the reaction was demonstrated, and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to provide desired β,γ-unsaturated esters in moderate to good yields. Moreover, α,β-unsaturated acids with a carbonyl group on the γ-position of acrylic acids also smoothly proceeded to furnish the desired products in good yields.

摘要

已开发出一种简便通用的方法,用于铜催化肉桂酸与2,2'-偶氮二(2-甲基丙酸)二甲酯的脱羧烷基羧化反应。证明了该反应的适用范围和通用性,芳环上带有供电子和吸电子基团的多种底物均与该反应兼容,能以中等至良好的产率提供所需的β,γ-不饱和酯。此外,在丙烯酸γ位带有羰基的α,β-不饱和酸也能顺利反应,以良好的产率得到所需产物。

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