苯亚磺酸钠和叔胺电化学耦合生成β-氨基乙烯砜  

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

作　　者：熊云奎[1,2] 张健叶 申裙 黄嘉宇 王涛 Xiong Yunkui;Zhang Jianye;Shen Qun;Huang Jiayu;Wang Tao(National Research Center for Carbohydrate Synthesis,Jiangxi Province Key Laboratory of Chemical Biology,Jiangxi Normal University,Nanchang 330022;College of Chemistry and Chemical Engineering,Jiangxi Normal university,Nanchang 330022)

机构地区：[1]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 [2]江西师范大学化学化工学院,南昌330022

出　　处：《有机化学》2021年第7期2735-2742,共8页Chinese Journal of Organic Chemistry

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.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.Only E-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.

关 键 词：β-氨基砜 β-氨基乙烯基砜 苯亚磺酸钠 叔胺 

分 类 号：TQ227.3[化学工程—有机化工]