大学化学 >> 2022, Vol. 37 >> Issue (7): 2111049.doi: 10.3866/PKU.DXHX202111049

化学实验 上一篇    下一篇

苯酚衍生物的电化学选择性C-H唑胺化反应研究

曹征, 林玲, 吴烟, 胡诗雨, 廖小建(), 冯鹏举()   

  • 收稿日期:2021-11-15 录用日期:2021-12-03 发布日期:2022-01-11
  • 通讯作者: 廖小建,冯鹏举 E-mail:tliaoxj@jnu.edu.cn;pfeng@jnu.edu.cn
  • 作者简介:Email: pfeng@jnu.edu.cn (冯鹏举)
    tliaoxj@jnu.edu.cn (廖小建)
    第一联系人:

    共同第一作者

  • 基金资助:
    基于学生综合素质和创新能力提升的实验实践教学体系改革(H20200510);中国高等教育学会2020年度“实验室管理研究”专项课题;广东省珠江人才计划青年拔尖人才(2017GC010302)

Study on Electrochemical Selective C-H Azolation of Phenol Derivatives

Zheng Cao, Ling Lin, Yan Wu, Shiyu Hu, Xiaojian Liao(), Pengju Feng()   

  • Received:2021-11-15 Accepted:2021-12-03 Published:2022-01-11
  • Contact: Xiaojian Liao,Pengju Feng E-mail:tliaoxj@jnu.edu.cn;pfeng@jnu.edu.cn

摘要:

电化学有机合成以电子为清洁的反应试剂,近年来得到快速发展。本实验以苯酚衍生物和唑类为原料通过电化学氧化实现脱氢偶联,构筑C-N键,合成唑胺化芳烃产物,继而探索反应的可重复性以及底物的兼容性,尝试建立适合本科创新实验研究的操作流程。实验涉及C-H官能团化反应,为当下有机合成科研前沿,反应操作简单,安全高效,反应时长可控,利用薄层色谱能方便监测反应的进程。产物可由硅胶柱层析法分离纯化,化合物结构可通过质谱、核磁共振波谱鉴定。该反应立足于绿色有机合成,综合应用有机化学与物理化学交叉学科知识,开发含氮化合物实用合成方法。

关键词: 电合成, C-N偶联, C-H官能化, 绿色化学, 唑胺化

Abstract:

Electrochemical organic synthesis uses electrons as clean reagents, and has developed rapidly in recent years. This research explores the phenol derivatives and azoles as raw materials to achieve dehydrogenation coupling through electrochemical oxidation, and the construction of C-N bonds for the synthesis of N-azolated aromatic products. Subsequently, the reproducibility of the reaction and the compatibility of substrate were studied to ultimately establish an operation process suitable for undergraduate innovative laboratory research. The experiment involves C-H functionalization reaction, which is the current frontier of organic synthesis scientific research. The reaction operation is simple, safe and efficient. Moreover, the reaction time is controllable via tuning the electricity. The reaction can be monitored by using thin-layer chromatography. The products can be separated and purified by silica gel column chromatography, and the structure can be analyzed by mass spectroscopy and nuclear magnetic resonance spectroscopy. The reaction is based on green organic synthesis to develop practical synthetic methods for nitrogen-containing compounds, by comprehensively applying cross-disciplinary knowledge of organic chemistry and physical chemistry.

Key words: Electrosynthesis, C-N coupling, C-H functionalization, Green chemistry, N-Azolation

MSC2000: 

  • G64