大学化学 >> 2026, Vol. 41 >> Issue (6): 136-144.doi: 10.12461/PKU.DXHX202510101

所属专题： 化学“101计划”案例

专题 上一篇    

离子液体中的Sonogashira偶联反应——化学“101计划”合成化学实验4.4D详解

侯雅君, 刘金鑫, 陈滔, 张艺, 周磊   

  1. 中山大学化学学院, 广东 广州 510006
  • 收稿日期:2025-10-28 录用日期:2026-01-05 发布日期:2026-06-18
  • 通讯作者: 周磊 E-mail:zhoul39@mail.sysu.edu.cn Lei Zhou
  • 基金资助:
    国家自然科学基金面上项目(22271318)；高等教育质量保障专项(化学“101计划”专项)

Sonogashira coupling reaction in ionic liquids: a detailed exploration of experiment 4.4D in the “101 Plan” synthetic chemistry curriculum

Yajun Hou, Jinxin Liu, Tao Chen, Yi Zhang, Lei Zhou   

  1. School of Chemistry, Sun Yat-sen University, Guangzhou 510006, Guangdong Province, China
  • Received:2025-10-28 Accepted:2026-01-05 Published:2026-06-18
  • Contact: Lei Zhou E-mail:zhoul39@mail.sysu.edu.cn

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摘要： “离子液体中的Sonogashira偶联反应”已被收录于最新出版的化学“101计划”《合成化学实验》教材中，归属于“4.4 金属催化偶联反应”这一章节。实验以Pd(PPh3)2Cl2为催化剂，商业可得的离子液体1-丁基-3-甲基咪唑六氟磷酸盐为溶剂，在无铜条件下实现4-甲基碘苯与苯乙炔的交叉偶联，以优异的产率得到内炔化合物。本实验包括简易氮气保护反应装置的搭建、微量注射器加样、薄层色谱检测反应、柱层析分离、旋转蒸发等实验操作。此外，要求学生根据所得的产率，计算反应的原子经济性、反应质量效率、原料回收率、过量物质的消耗，并将结果绘制于一个雷达五边形图中。本文对该实验的背景知识做了补充介绍，详细分析了实验过程中的注意事项，给出了实验实施安排的建议，并提供了数据分析和思考题的参考答案。

关键词: Sonogashira偶联, 离子液体, 金属催化, 炔烃, 绿色化学

Abstract: The “Sonogashira Coupling Reaction in Ionic Liquid” experiment has been incorporated into the recently published “Synthetic Chemistry Experiments” textbook as part of the Chemistry “101 Plan” series, specifically within Chapter 4.4 on metal-catalyzed coupling reactions. This experiment employs Pd(PPh3)2Cl2 as the catalyst and commercially available 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid as the solvent to achieve copper-free cross-coupling between 4-iodotoluene and phenylacetylene, yielding the internal alkyne product with excellent efficiency. The experimental procedure encompasses several fundamental techniques: setup of the basic nitrogen-protected reaction apparatus, precise reagent addition using microliter syringes, reaction monitoring via thin-layer chromatography, product isolation through column chromatography, and rotary evaporation operations. Furthermore, students are required to perform comprehensive reaction analysis by calculating atom economy, reaction mass efficiency, material recovery parameter, and inverse stoichiometric factor based on the obtained yield, with subsequent visualization of these metrics in a pentagonal radar plot. This article supplements the experimental protocol with essential background information, detailed analysis of critical experimental considerations, practical implementation suggestions, and reference solutions for data analysis and discussion questions.

Key words: Sonogashira coupling, Ionic liquid, Metal catalysis, Alkynes, Green chemistry