Home

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.
1. [1]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
2. [2]
  Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
3. [3]
  Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
4. [4]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
5. [5]
  Ranhui Fu , Shixin Zhou , Ran Ji , Feifei Gao , Hui Xu . 季膦盐合成实验的改进与拓展——水相一步法合成乙基三苯基溴化膦及其力致发光锰配合物的制备及表征. University Chemistry, 2026, 41(5): 252-263. doi: 10.12461/PKU.DXHX202510018
6. [6]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
7. [7]
  Renxiu Zhang , Xin Zhao , Yunfei Zhang . Application of Electrochemical Synthesis in the Teaching of Organic Chemistry. University Chemistry, 2025, 40(4): 174-180. doi: 10.12461/PKU.DXHX202406116
8. [8]
  Zhanhong Tong , Xiaoyu Xie , Fangfang Chen . Appreciating Autumn Leaves: A Brief Analysis of the Causes behind “Frost Leaves Redder than February Flowers”. University Chemistry, 2024, 39(9): 183-188. doi: 10.12461/PKU.DXHX202404005
9. [9]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
10. [10]
  Zhiqiang Hao , Jinyue Li , Shiqi Zhang , Yujia Hou , Helue Sun . 维生素B₂促进的光催化氧化合成二苯甲酮. University Chemistry, 2026, 41(5): 350-357. doi: 10.12461/PKU.DXHX202510080
11. [11]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
12. [12]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
13. [13]
  Renyi Shao , Khurram Abbas , Vladimir Yu. Osipov , Haimei Zhu , Yuan Li , Usama , Hong Bi . Red-emitting carbon dots prepared from Epipremnum Aureum leaves extract for biological imaging. Acta Physico-Chimica Sinica, 2026, 42(2): 100134-0. doi: 10.1016/j.actphy.2025.100134
14. [14]
  Xiaomei Ai , Muran Lin , Jinlan Zeng , Jiwei Ren . 可见光催化绿色合成二肽化合物. University Chemistry, 2026, 41(5): 358-367. doi: 10.12461/PKU.DXHX202510007
15. [15]
  Haolin Yang , Aoxiang Fan , Yi Song , Yang Chen . 基于甲酰化-共轭脱氢串联策略的苯并呋喃-5-甲醛的制备——推荐一个基础有机合成综合性教学实验. University Chemistry, 2026, 41(5): 141-148. doi: 10.12461/PKU.DXHX202511156
16. [16]
  Xinran Han , Jiaxin Li , Yuhan Kang , Qiongyou Wu . 虚实融合驱动的绿色杀菌剂苯醚唑酰胺创制实验设计. University Chemistry, 2026, 41(5): 422-429. doi: 10.12461/PKU.DXHX202511113
17. [17]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
18. [18]
  Ruoxi RUN , Jikai ZHU , Lixia HAN , Zhiyin XIAO , Xiujuan JIANG , Jing JIN . Red light-induced CO-release from manganese carbonyl complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2575-2583. doi: 10.11862/CJIC.20250132
19. [19]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
20. [20]
  Bingliang Li , Yuying Han , Dianyang Li , Dandan Liu , Wenbin Shang . One-Step Synthesis of Benorilate Guided by Green Chemistry Principles and in vivo Dynamic Evaluation. University Chemistry, 2024, 39(6): 342-349. doi: 10.3866/PKU.DXHX202311070

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(590)
HTML views(58)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return