Citation: Yajun Hou, Jinxin Liu, Tao Chen, Yi Zhang, Lei Zhou. Sonogashira coupling reaction in ionic liquids: a detailed exploration of experiment 4.4D in the “101 Plan” synthetic chemistry curriculum[J]. University Chemistry, ;2026, 41(6): 136-144. doi: 10.12461/PKU.DXHX202510101 shu

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

School of Chemistry, Sun Yat-sen University, Guangzhou 510006, Guangdong Province, China

Corresponding author: Lei Zhou, zhoul39@mail.sysu.edu.cn
Received Date: 28 October 2025
Revised Date: 5 January 2026

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.
- Sonogashira coupling,
- Ionic liquid,
- Metal catalysis,
- Alkynes,
- Green chemistry
1. [1]
  P. Biffis, A. Centomo, A. Del Zotto, M. Zecca, Chem. Rev. 2018, 118, 2249.
2. [2]
  C.C.C. Johansson Seechurn, M.O. Kitching, T.J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 2012, 51, 5062.
3. [3]
  K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467.
4. [4]
  R. Chinchilla, C. Nájera, Chem. Soc. Rev. 2011, 40, 5084.
5. [5]
  S.H. Chanteau, J.M. Tour, J. Org. Chem. 2003, 68, 8750.
6. [6]
  F. Diederich, P.J. Stang, R.R. Tykwinski, Acetylene Chemistry. Chemistry, Biology and Material Science, WILEY-VCH: Weinheim, Germany, 2005.
7. [7]
  H. Yang, S. Tao, S. He, D. Jiang, J. Am. Chem. Soc. 2025, 147, 19667.
8. [8]
  M. Trunk, A. Herrmann, H. Bildirir, A. Yassin, J. Schmidt, A. Thomas, Chem. Eur. J. 2016, 22, 7179.
9. [9]
  J. Bailey, E.L. Byrne, P. Goodrich, P. Kavanagha, M. Swadźba-Kwaśny, Green Chem. 2024, 26, 1092.
10. [10]
  P.T. Anastas, M.M. Kirchhoff, Acc. Chem. Res. 2002, 35, 686.
11. [11]
12. [12]
  F. Mohajer, M.M. Heravi, V. Zadsirjan, N. Poormohammad, RSC Adv. 2021, 11, 6885.
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