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Citation: Tao Cao, Fang Fang, Nianguang Li, Yinan Zhang, Qichen Zhan. Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates[J]. University Chemistry, ;2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098 shu

Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates

College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China

Received Date: 28 September 2023
Revised Date: 15 January 2024

Visible light irradiation is a crucial factor in modern synthetic organic chemistry, yet it is often overlooked in undergraduate organic experiment textbooks. This innovative experiment introduces a microscale approach, inspired by the principles of photosynthesis, to catalyze the oxidation of p-cyanophenylboronic acid to p-hydroxybenzonitrile using extracts from spinach leaves under red-light irradiation. The incorporation of this comprehensive experiment into our school’s organic chemistry laboratory teaching offers several advantages: (1) The environmentally friendly catalyst is easily accessible, and the synthesis process is safe and reliable with low experimental costs. (2) Microscale experiments contribute to reducing environmental pollution, enhancing laboratory safety, saving reagents and time, minimizing instrument wear and tear, and fostering students’ meticulous experimental style and habits. (3) Beyond expanding students’ knowledge and horizons, this experiment also ignites their interest in learning and boosts their learning enthusiasm.
- Spinach leaves,
- Chlorophyll,
- Red light,
- p-Hydroxybenzonitrile,
- Green synthesis
1. [1]
2. [2]
3. [3]
4. [4]
  Cheung, K. P. S.; Sarkar, S.; Gevorgyan, V. Chem. Rev. 2022, 122 (2), 1543.
5. [5]
  Bellotti, P.; Huang, H.-M.; Faber, T.; Glorius, F. Chem. Rev. 2023, 123 (8), 4237.
6. [6]
  Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116 (17), 10075.
7. [7]
  Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81 (16), 6898.
8. [8]
9. [9]
  Cui, W. W.; Li, X. F.; Guo, G. J.; Song, X. Y.; Lv, J.; Yang. D. S. Org. Lett. 2022, 24 (29), 5391.
10. [10]
  Senecal, T. D.; Shu, W.; Buchwald, S. L. Angew. Chem. Int. Ed. 2013, 52 (38), 10035.
11. [11]
  Yan, P.; Zeng, R.; Bao, B.; Yang, X.-M.; Zhu, L.; Pan, B.; Niu, S.-L.; Qi, X.-W.; Li, Y.-L.; Ouyang, Q. Green Chem. 2022, 24 (23), 9263.
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