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芳基环氧化合物的电化学羧化反应与 CO 用于 β-羟基酸的简便和选择性合成。

Electrocarboxylation of Aryl Epoxides with CO for the Facile and Selective Synthesis of β-Hydroxy Acids.

机构信息

State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin, 300071, China.

出版信息

Angew Chem Int Ed Engl. 2022 Sep 19;61(38):e202207746. doi: 10.1002/anie.202207746. Epub 2022 Aug 17.

Abstract

Herein, an efficient and facile approach to valuable β-hydroxy acid derivatives from readily available aryl epoxides and CO with high chemo- and regioselectivity under mild and sustainable electrochemical conditions is described. This approach showed broad substrate scope and good functional-group compatibility. In addition to aryl epoxides, four- to six-membered aryl cyclic ethers could all be tolerated in the reaction to provide synthetically useful hydroxy acids with high efficiency. Further late-stage carboxylation of complex molecules and drug derivatives demonstrated its potential application in the pharmaceutical industry. Mechanistic studies disclosed possible reaction pathways.

摘要

本文描述了一种在温和可持续的电化学条件下,从易得的芳基环氧化物和 CO 高效、简便地制备有价值的β-羟基酸衍生物的方法,具有高的化学和区域选择性。该方法具有广泛的底物范围和良好的官能团兼容性。除了芳基环氧化物,四到六元芳基环醚在反应中也能被容忍,以高效提供具有高合成价值的羟基酸。此外,复杂分子和药物衍生物的后期羧化反应进一步证明了其在制药工业中的潜在应用。机理研究揭示了可能的反应途径。

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