大学化学 >> 2023, Vol. 38 >> Issue (9): 263-271.doi: 10.3866/PKU.DXHX202212027

化学实验 上一篇    下一篇

对乙基苯甲醚的电化学苄位唑胺化反应的探索

胡新伟, 阮志雄()   

  • 收稿日期:2022-12-11 录用日期:2023-03-10 发布日期:2023-03-20
  • 通讯作者: 阮志雄 E-mail:zruan@gzhmu.edu.cn
  • 基金资助:
    国家自然科学基金(22271067);2023年广医大一流专业建设项目-药学院-教学改革研究项目(02-408-2304-13039XM)

Benzylic C―H Azolation of p-Ethyl Anisole by Electro-Oxidation

Xinwei Hu, Zhixiong Ruan()   

  • Received:2022-12-11 Accepted:2023-03-10 Published:2023-03-20
  • Contact: Zhixiong Ruan E-mail:zruan@gzhmu.edu.cn

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摘要：

本实验以对乙基苯甲醚和5-苯基四氮唑为原料通过电化学氧化实现烷基与胺的脱氢偶联反应合成2-(1-(4-甲氧基苯基)乙基)-5-苯基-2H-四氮唑产物，构筑C―N键，探究含氮化合物的新型合成方法。反应操作简单、安全高效，同时还将绿色化学理念融入到有机合成方法学的实验过程中。作为本科教学实验，该实验不仅涉及多种有机实验的基本操作，还包含了反应监测、分离纯化、结构表征等重要环节。以本实验方案为蓝本，结合有关碳氢键活化反应研究进展的微课学习和拓展练习，以及在综合实验中添加趣味实验，实现理论与实践的有效互动，提升化学和药学等专业本科生解决较为复杂有机合成问题的综合能力，进一步夯实化学类人才的研究基础。

关键词: 电化学氧化, 脱氢偶联反应, 唑胺化, 绿色化学, 教学实验

Abstract:

In this experiment, the dehydrogenative coupling of p-ethyl anisole and 2-(1-(4-methoxyphenyl)ethyl)-5-phenyl-2H-tetrazole is realized through electro-oxidation to generate C―N bonds and synthesize a benzyl-azolated aromatic product. The reaction is simple, safe, and efficient. It also integrates the experimental exploration of green chemistry concepts and organic synthetic methodology. As an undergraduate teaching experiment, it not only covers the basic operation of various organic experiments, but also includes reaction monitoring, purification, structural characterization, and other important procedures. Using this experimental protocol, micro-class learning, extended exercises on the progress of C―H activation, interesting experiments, as well as effective synergy of theoretical knowledge and synthetic practice are realized. Thus, the comprehensive ability of undergraduates majoring in chemistry and pharmacy to solve complex organic synthesis problems is improved, and the research foundation to nurture chemistry talents is further established.

Key words: Electrochemical oxidation, Dehydrogenative coupling reaction, Azolation, Green chemistry, Teaching experiment