大学化学 >> 2021, Vol. 36 >> Issue (4): 2005019.doi: 10.3866/PKU.DXHX202005019

化学实验 上一篇    下一篇

可见光诱导的2, 2-二(1H-吲哚-3-基)乙酸乙酯的合成——推荐一个绿色有机化学实验

李立奇, 杨枭荣, 张元()   

  • 收稿日期:2020-05-07 录用日期:2020-06-22 发布日期:2020-07-06
  • 通讯作者: 张元 E-mail:zhangyuan@lzu.edu.cn
  • 作者简介:张元, Email: zhangyuan@lzu.edu.cn

Visible Light-Induced Synthesis of Ethyl 2, 2-Di(1H-indol-3-yl) acetate: Recommendation of a Green Organic Chemistry Experiment

Liqi Li, Xiaorong Yang, Yuan Zhang()   

  • Received:2020-05-07 Accepted:2020-06-22 Published:2020-07-06
  • Contact: Yuan Zhang E-mail:zhangyuan@lzu.edu.cn

摘要:

可见光催化由于其清洁、高效、反应条件温和等优点,近年来已在有机合成领域得到广泛应用。但是目前可见光催化的反应尚未在本科生实验教学中得以推广。3,3'-二吲哚基甲烷骨架广泛存在于药物分子结构中,其也可以作为生物碱类天然产物合成的重要中间体。最近,我们发展了一种通过可见光诱导的甘氨酸衍生物与吲哚间的需氧脱氢偶联反应来合成3,3'-二吲哚基甲烷的方法。在此工作的基础上,我们设计了一个以N-(4-甲氧基苯基)甘氨酸乙酯和吲哚为原料,以罗丹明6G为光催化剂,在可见光照射、室温条件下高效合成2,2-二(1H-吲哚-3-基)乙酸乙酯的半微量绿色有机化学实验,目的在于通过将前沿科研内容引入实验教学,进一步促使大学生开拓知识视野、树立“绿色化学”理念和环保意识。

关键词: 光催化, 2, 2-二(1H-吲哚-3-基)乙酸乙酯, 绿色化学, 本科生实验教学

Abstract:

Owing to its mild, clean, and environmentally benign characteristics, visible light-induced photoredox catalysis in the past few years has emerged as a powerful tool to trigger organic transformations; however, it has not been introduced into the undergraduate laboratory teaching. 3, 3'-Bisindolylmethanes (BIMs) are privileged structural units that exist widely in numerous pharmaceutical active molecules. Moreover, BIMs are also important synthetic intermediates of numerous alkaloid natural products. Recently, we developed a visible light-induced aerobic oxidative cross-coupling reaction of glycine derivatives with indoles, which provides a straightforward access to BIMs. On the basis of this work, we designed a semi-microscale organic chemistry experiment for the efficient synthesis of ethyl 2, 2-di (1H-indol-3-yl) acetate, starting from ethyl (4-methoxyphenyl) glycinate and indole by using Rhodamine 6G as the photocatalyst under the irradiation of visible light at room temperature. The aims are to promote students to broaden their horizon of knowledge, establish the concept of "green chemistry" and awareness of environmental protection through the introduction of innovative scientific research into the laboratory teaching.

Key words: Photoredox catalysis, Ethyl 2, 2-di(1H-indol-3-yl) acetate, Green chemistry, Undergraduate laboratory teaching

MSC2000: 

  • G64