大学化学 >> 2022, Vol. 37 >> Issue (12): 2112020.doi: 10.3866/PKU.DXHX202112020

化学实验 上一篇    下一篇

实验教学与绿色化学的融合——一个绿色Suzuki-Miyaura交叉偶联反应教学实验研究

王艳艳, 高玲香, 张伟强, 顾泉, 简亚军, 高子伟()   

  • 收稿日期:2021-12-07 录用日期:2022-03-10 发布日期:2022-03-25
  • 通讯作者: 高子伟 E-mail:zwgao@snnu.edu.cn
  • 作者简介:高子伟, Email: zwgao@snnu.edu.cn
  • 基金资助:
    国家自然科学基金(面上项目)(21771122);陕西师范大学中央高校基本科研业务费专项资金项目(GK202103027)

Integrating Green Chemistry into Teaching Laboratories: A Teaching Research on Green Suzuki-Miyaura Cross-Coupling Reaction

Yanyan Wang, Lingxiang Gao, Weiqiang Zhang, Quan Gu, Yajun Jian, Ziwei Gao()   

  • Received:2021-12-07 Accepted:2022-03-10 Published:2022-03-25
  • Contact: Ziwei Gao E-mail:zwgao@snnu.edu.cn

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摘要：

Suzuki-Miyaura交叉偶联反应是现代合成化学中一个重要反应，广泛应用于药物、天然产物、染料等化合物的合成。受限于催化剂价格高昂、反应操作复杂等原因，涉及该反应的实验难以在本科生教学实验中推广。本文介绍了一种绿色钯催化Suzuki-Miyaura交叉偶联反应的有机合成实验。催化剂无需制备且钯用量少，并可被多次循环利用，解决了实验成本问题；该实验中的溶剂为水、反应条件温和、反应速率快、产物分离便捷，展示了绿色化学的安全优势，可引入高年级本科课程。本实验中，学生既可以学习诺贝尔奖级有机合成反应，又可以通过对催化剂的回收再利用和对反应的绿色评估，体会到绿色化学在过渡金属催化有机反应中的节能减排和可持续发展优势。

关键词: 绿色化学, Suzuki-Miyaura交叉偶联反应, 水相, 可循环催化剂, 本科生实验教学

Abstract:

The Suzuki-Miyaura cross-coupling reaction is a powerful tool for organic transformations and has been widely used in the synthesis of drugs, natural products, dyes, etc. However, this reaction has not been promoted in undergraduate laboratories due to the expense of the catalyst and the complexity of the reaction. Herein, we present a green organic synthesis experiment utilizing recyclable, commercially available tetraamminepalladium chloride as a catalyst in the Suzuki-Miyaura cross-coupling reaction, significantly reducing experimental costs. Furthermore, this experiment has the advantages of mild reaction conditions, a fast reaction rate, convenient product separation, and the use of water as a solvent, demonstrating the safety benefits of green chemistry and rendering it suitable for integration into an upper-division undergraduate course. While engaging with a Nobel Prize-winning organic synthesis reaction, students will gain an appreciation for green chemistry and catalyst recycling in traditional metal-catalyzed organic reactions, and the advantages in terms of energy savings, emission reduction, and sustainable development.

Key words: Green chemistry, Suzuki-Miyaura cross-coupling reaction, Water, Recyclable catalyst, Undergraduate laboratory teaching