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

引用本文: 郭维斯, 王书文, 李明. 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[J]. 大学化学, 2023, 38(5): 157-162. doi: 10.3866/PKU.DXHX202206050 shu

Citation: Weisi Guo, Shuwen Wang, Ming Li. Electrochemical Reduction of Phenyl Sulfoxide to Diphenyl Sulfide: A Semi-Microscale Green Organic Chemistry Experiment is Recommended[J]. University Chemistry, 2023, 38(5): 157-162. doi: 10.3866/PKU.DXHX202206050 shu

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

青岛科技大学化学与分子工程学院, 山东青岛 266042

通讯作者: 郭维斯, wsguo@qust.edu.cn

基金项目:
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)

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:

English

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

College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, Shandong Province, China

Corresponding author: Weisi Guo, wsguo@qust.edu.cn

Received Date: 16 June 2022

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:

1. [1]
  Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
2. [2]
  Zhang, W.; Lu, L.; Zhang, W.; Wang, Y.; Ware, S. D.; Mondragon, J.; Rein, J.; Strotman, N.; Lehnherr, D.; Lin, S.; et al. Nature 2022, 604, 292.Zhang, W.; Lu, L.; Zhang, W.; Wang, Y.; Ware, S. D.; Mondragon, J.; Rein, J.; Strotman, N.; Lehnherr, D.; Lin, S.; et al. Nature 2022, 604, 292.
3. [3]
  Gnaim, S.; Bauer, A.; Zhang, H.; Chen, L.; Gannett, C.; Malapit, C. A.; Hill, D. E.; Vogt, D.; Tang, T.; Baran, P. S.; et al. Nature 2022, 605, 687.Gnaim, S.; Bauer, A.; Zhang, H.; Chen, L.; Gannett, C.; Malapit, C. A.; Hill, D. E.; Vogt, D.; Tang, T.; Baran, P. S.; et al. Nature 2022, 605, 687.
4. [4]
  Hamby, T. B.; LaLama, M. J.; Sevov, C. S. Science 2022, 376, 410.Hamby, T. B.; LaLama, M. J.; Sevov, C. S. Science 2022, 376, 410.
5. [5]
  赵梦龙, 苑岱雷, 叶梓, 房芳, 于月娜. 大学化学, 2022, 37 (5), 2109108.
6. [6]
  李明, 郭维斯, 王书文, 刘永军, 张林宝, 辛飞飞. 有机化学实验. 北京:科学出版社, 2019:181-184.
7. [7]
  Wang, N.; Saidhareddy, P.; Jiang, X. Nat. Prod. Rep. 2020, 37, 246.Wang, N.; Saidhareddy, P.; Jiang, X. Nat. Prod. Rep. 2020, 37, 246.
8. [8]
  Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.
9. [9]
  王明, 王翠红, 姜雪峰. 有机化学, 2019, No. 39, 2139.
10. [10]
  李伟林, 陈炫颖, 郑天骄, 邹祺, 陈文博. 有机化学, 2019, No. 39, 2443.
11. [11]
  Fujita, S.; Yamaguchi, S.; Yamazoe, S.; Yamasaki, J.; Mizugaki, T.; Mitsudome, T. Org. Biomol. Chem. 2020, 18, 8827.Fujita, S.; Yamaguchi, S.; Yamazoe, S.; Yamasaki, J.; Mizugaki, T.; Mitsudome, T. Org. Biomol. Chem. 2020, 18, 8827.
12. [12]
  Clarke, A. K.; Parkin, A.; Taylor, R.; Unsworth, W. P.; Rossi-Ashton, J. A. ACS Catal. 2020, 10, 5814.Clarke, A. K.; Parkin, A.; Taylor, R.; Unsworth, W. P.; Rossi-Ashton, J. A. ACS Catal. 2020, 10, 5814.
13. [13]
  Kong, Z.; Pan, C.; Li, M.; Wen, L.; Guo, W. Green Chem. 2021, 23, 2773.Kong, Z.; Pan, C.; Li, M.; Wen, L.; Guo, W. Green Chem. 2021, 23, 2773.

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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

通讯作者: 郭维斯, wsguo@qust.edu.cn

English

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

Corresponding author: Weisi Guo, wsguo@qust.edu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

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

通讯作者: 郭维斯, wsguo@qust.edu.cn

English

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

Corresponding author: Weisi Guo, wsguo@qust.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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