研究论文

碱性离子液体中吲哚与芳基硫酚的3-芳烃硫基化反应

  • 岑竞鹤 ,
  • 杨凯 ,
  • 李建晓 ,
  • 李灿 ,
  • 杨少容
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  • a 华南理工大学化学与化工学院 广州 510640;
    b 赣南医学院药学院 赣州 341000

收稿日期: 2017-07-05

  修回日期: 2017-08-16

  网络出版日期: 2017-08-18

基金资助

国家自然科学基金(Nos.21502055,21642005)、中央高校基本科研业务费(No.2015ZM150)和中国博士后科学基金(No.2016T90779)资助项目.

Direct 3-Arylsulfenylation of Indoles with Thiols in Basic Ionic Liquid

  • Cen Jinghe ,
  • Yang Kai ,
  • Li Jianxiao ,
  • Li Can ,
  • Yang Shaorong
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  • a School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640;
    b School of Pharmaceutical Sciences, Gannan Medical University, Ganzhou 341000

Received date: 2017-07-05

  Revised date: 2017-08-16

  Online published: 2017-08-18

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21502055, 21642005), the Fundamental Research Funds for the Central Universities (No. 2015ZM150) and the China Postdoctoral Science Foundation (No. 2016T90779).

摘要

无金属条件下,在离子液体[Hemim]N(CN)2中,实现了吲哚衍生物与芳基硫酚的偶联反应,以中等至优良产率(68%~90%)合成系列芳烃硫基取代的吲哚化合物.其结构均经1H NMR,13C NMR及HRMS确证.该反应具有反应条件温和、底物适用范围广、环境友好等优点.此外,生成的产物通过进一步的修饰与转化可以衍生为结构复杂的、具有潜在生物活性的有机分子骨架结构.

本文引用格式

岑竞鹤 , 杨凯 , 李建晓 , 李灿 , 杨少容 . 碱性离子液体中吲哚与芳基硫酚的3-芳烃硫基化反应[J]. 有机化学, 2017 , 37(12) : 3213 -3219 . DOI: 10.6023/cjoc201707005

Abstract

An efficient and convenient transition metal-free procedure for the synthesis of 3-sulfenylindoles derivatives in moderate to good yields from readily available indoles and thiols in basic ionic liquid has been developed. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. This sulfenylation process provides a novel route for directly accessing 3-sulfenylindoles in good to excellent yields and good functional group tolerance with high atom efficiency. Notably, the current methodology could also be conveniently applied to the synthesis of thioarylated naturally occurring biologically active frameworks.

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