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2023 , Vol. 43 >Issue 2: 756 - 762

DOI: https://doi.org/10.6023/cjoc202206023

研究简报

α-酮酸与硫酚的电化学脱羧偶联: 一种合成硫代酸酯的新方法

  • 黄嘉为 ,
  • 李潇漫 ,
  • 徐亮 ,
  • 韦玉
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  • 石河子大学化学化工学院 新疆兵团化工绿色过程重点实验室 新疆石河子 832003

收稿日期: 2022-09-06

  修回日期: 2022-09-21

  网络出版日期: 2022-11-01

基金资助

国家自然科学基金(22061036)

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Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters

  • Jiawei Huang ,
  • Xiaoman Li ,
  • Liang Xu ,
  • Yu Wei
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  • Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003
* Corresponding author. E-mail:

Received date: 2022-09-06

  Revised date: 2022-09-21

  Online published: 2022-11-01

Supported by

National Natural Science Foundation of China(22061036)

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摘要

在生物活性分子、天然产物和有机材料的合成中, 硫酯类化合物为常见的反应中间体. 近些年来, α-酮酸与硫醇或硫酚的脱羧偶联成为合成该类化合物的新方法, 实现了电化学条件下α-酮酸与硫酚的脱羧偶联反应, 以中等至良好的收率得到硫酯类化合物. 该方法操作简便, 无需传统方法中的常用的金属催化剂、碱或外部氧化剂, 为硫酯类化合物的合成提供了一条温和、绿色的新路径.

关键词： 电化学合成; α-酮酸; 硫酚; 硫酯

本文引用格式

黄嘉为 , 李潇漫 , 徐亮 , 韦玉 . α-酮酸与硫酚的电化学脱羧偶联: 一种合成硫代酸酯的新方法[J]. 有机化学, 2023 , 43(2) : 756 -762 . DOI: 10.6023/cjoc202206023

Abstract

Thioester compounds have been widely applied in the synthesis of bioactive chemicals, natural products and organic materials due to their versatile reactivities. In recent years, the decarboxylation coupling reactions between α-keto acids and thiols/thiophenols have been utilized to access thioesters. Herein, an electrochemical decarboxylation coupling method has been established, which uses α-keto acids and thiophenols as the starting materials and affords thioesters in moderate to good yields. This protocol features simple manipulation and avoids usually needed metal-based catalysts, bases or external oxidants, thus providing a new, mild, and green pathway to synthesize thioester compounds.

Key words： electrochemical synthesis; α-keto acid; thiophenol; thioester

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