大学化学 >> 2023, Vol. 38 >> Issue (5): 157-162.doi: 10.3866/PKU.DXHX202206050

化学实验 上一篇    下一篇

电化学促进的二苯基亚砜还原制备二苯基硫醚——推荐一个半微量绿色有机化学实验

郭维斯(), 王书文, 李明   

  • 收稿日期:2022-06-16 录用日期:2022-08-19 发布日期:2022-09-02
  • 通讯作者: 郭维斯 E-mail:wsguo@qust.edu.cn

Electrochemical Reduction of Phenyl Sulfoxide to Diphenyl Sulfide: A Semi-Microscale Green Organic Chemistry Experiment is Recommended

Weisi Guo(), Shuwen Wang, Ming Li   

  • Received:2022-06-16 Accepted:2022-08-19 Published:2022-09-02
  • Contact: Weisi Guo E-mail:wsguo@qust.edu.cn

摘要:

有机电合成具有绿色、高效、可控等优点,近年来已成为有机合成发展的热点领域。但是有机电合成反应目前尚未在本科生有机化学实验教学中予以推广。硫醚化合物广泛存在于天然产物和药物活性分子中,也是有机合成的重要中间体,传统合成方法需要使用还原剂且反应条件剧烈,最近我们发展了一种电化学促进亚砜还原的新方法来合成硫醚化合物,在此基础上,设计了一个以易得的二苯基亚砜为原料,在电化学促进室温条件下合成二苯基硫醚的绿色有机化学实验。本实验通过将科研成果转化为有机化学实验教学,有助于激发学生的创新意识,树立“绿色合成”理念。

关键词: 有机电合成, 还原反应, 绿色化学, 硫醚

Abstract:

Organic electrosynthesis is an emerging field of organic synthesis because its controllability, efficiency, and "green" profile. However, electrochemical synthesis has not yet been implemented in the organic chemistry laboratory curriculum for undergraduates. Organic sulfides are widely present in natural products and bioactive molecules. They are also important intermediates in organic synthesis. Most traditional methods for the preparation of these species require reductants and harsh reaction conditions. Recently, we reported the facile electrochemical reduction of sulfoxides to sulfides under mild reaction conditions. Subsequently, we designed a "green" electrochemical protocol for the efficient synthesis of diphenyl sulfide, from readily available phenyl sulfoxide, at room temperature. This experiment aimed to establish the concept of "green" synthesis amongst the undergraduate student population.

Key words: Organic electrosynthesis, Reduction, Green chemistry, Sulfide