大学化学 >> 2025, Vol. 40 >> Issue (1): 303-308.doi: 10.12461/PKU.DXHX202404111

所属专题: 有机电化学

化学实验 上一篇    下一篇

电化学还原苯并噻吩衍生物

薄世捷, 郭维斯, 王书文, 宋然, 李明, 张林宝   

  1. 青岛科技大学化学与分子工程学院, 山东 青岛 266042
  • 收稿日期:2024-04-18 录用日期:2024-06-03 发布日期:2025-01-06
  • 通讯作者: 张林宝 E-mail:zhang_linbao@126.com
  • 基金资助:
    青岛科技大学一流本科课程建设项目(2021020);山东省一流本科课程建设项目(2021309)

Electrochemical Reduction of Benzothiophene Derivatives

Shijie Bo, Weisi Guo, Shuwen Wang, Ran Song, Ming Li, Linbao Zhang   

  1. College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, Shandong Province, China
  • Received:2024-04-18 Accepted:2024-06-03 Published:2025-01-06
  • Contact: Linbao Zhang E-mail:zhang_linbao@126.com

摘要: 有机电合成是一种绿色、温和、高效的合成方法,但其在本科有机实验教学中并未有效推广。二氢苯并噻吩衍生物广泛存在于生物活性化合物中,在医药行业有重要的应用价值。对苯并噻吩衍生物进行加氢还原是获得该类化合物最简单直接的方法,但传统的还原方法存在诸多缺陷。最近,我们建立了一种电化学促进的苯并噻吩衍生物的还原方法,该方法以电子作为还原剂,六氟异丙醇作为氢供体。在此基础上,设计了一个对苯并噻吩砜进行电化学还原制备2,3-二氢苯并[b]噻吩1,1-二氧化物的有机化学实验。

关键词: 有机电合成, 还原反应, 苯并噻吩衍生物

Abstract: Organic electrosynthesis is a green, mild, and efficient synthesis method, but it has not been effectively promoted in undergraduate organic experimental teaching. Dihydrobenzothiophene derivatives are widely found in biologically active compounds and have important application value in the pharmaceutical industry. Hydrogenation reduction of benzothiophene derivatives is the simplest and most direct method to obtain such compounds, but traditional reduction methods have many shortcomings. We developed an electrochemical-promoted reduction method of benzothiophene derivatives using electrons as the reducing agent and hexafluoroisopropanol as the hydrogen donor. On this basis, an organic chemistry experiment was designed to prepare 2,3-dihydrobenzo[b]thiophene 1,1-dioxide by electrochemical reduction of benzothiophene sulfone.

Key words: Organic electrosynthesis, Reduction reaction, Benzothiophene derivatives