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2021 , Vol. 41 >Issue 7: 2735 - 2742

DOI: https://doi.org/10.6023/cjoc202012051

研究论文

苯亚磺酸钠和叔胺电化学耦合生成β-氨基乙烯砜

  • 熊云奎 ,
  • 张健叶 ,
  • 申裙 ,
  • 黄嘉宇 ,
  • 王涛
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  • a 江西师范大学 国家单糖化学合成工程技术研究中心 南昌 330022
    b 江西师范大学化学化工学院 南昌 330022

收稿日期: 2020-12-30

  修回日期: 2021-03-07

  网络出版日期: 2021-04-16

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Electrochemical Coupling of the Sulfonic Acid Sodium and Tertiary Amines for the Synthesis ofβ-Amidovinyl Sulfones

  • Yunkui Xiong ,
  • Jianye Zhang ,
  • Qun Shen ,
  • Jiayu Huang ,
  • Tao Wang
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  • a National Research Center for Carbohydrate Synthesis, Jiangxi Province Key Laboratory of Chemical Biology,Jiangxi Normal University, Nanchang 330022
    b College of Chemistry and Chemical Engineering, Jiangxi Normal university, Nanchang 330022
* Corresponding authors. E-mail: ;

Received date: 2020-12-30

  Revised date: 2021-03-07

  Online published: 2021-04-16

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摘要

β-氨基砜是一种特别有用的生物活性分子的骨架.β-氨基乙烯基砜加氢法是合成β-氨基砜的一种简便、高效的方法. 提出了一种以苯亚磺酸钠和叔胺为底物的电化学法合成β-氨基乙烯基砜. 在无金属催化剂和无氧化剂的条件下, 仅合成E构型的β-氨基乙烯基砜. 循环伏安实验和对照实验表明, 该电合成反应经历了磺酸自由基与烯胺的加成, 并生成碳自由基的过程.

关键词： β-氨基砜; β-氨基乙烯基砜; 苯亚磺酸钠; 叔胺

本文引用格式

熊云奎 , 张健叶 , 申裙 , 黄嘉宇 , 王涛 . 苯亚磺酸钠和叔胺电化学耦合生成β-氨基乙烯砜[J]. 有机化学, 2021 , 41(7) : 2735 -2742 . DOI: 10.6023/cjoc202012051

Abstract

β-Amido sulfone motif reprents a particularly useful scaffold for the biologically active molecules. The hydrogenation ofβ-amidovinyl sulfon is an alternative method to synthesizeβ-amido sulfone. Herein, one electrochemical method to synthesizeβ-amido sulfone using sodium sulfites and tertiary amines as substrates is presented. OnlyE-configurations ofβ-amidovinyl sulfonyl were synthesized under metal catalyst- and oxidant-free condition. Cyclic voltammetry (CV) and control experiments indicate that this electrosynthesis reaction goes through a radical process which the sulfonyl radical adds to enamine to form the carbon radical.

Key words： β-amido sulfone; β-amidovinyl sulfon; sodium sulfites; tertiary amines

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