Citation:
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[J]. University Chemistry,
;2024, 39(5): 296-306.
doi:
10.3866/PKU.DXHX202311087
-
This experiment introduces undergraduate students to the forefront of organic chemistry and new synthetic methodologies through the synthesis of isoquinolinone guided by photochemistry. By integrating organic photochemistry and continuous flow chemistry, the experiment aims to broaden the scope of undergraduate organic chemistry laboratory teaching. Carbon nitride (g-C3N4) is employed as a heterogeneous photocatalyst, while oxygen serves as a safe and atom-economic oxidant, enabling the synthesis of isoquinolinone under visible-light irradiation in a continuous flow setup. The experiment encompasses both batch and continuous flow photochemical synthesis of isoquinolinone, as well as the preparation of the natural product corydaldine. Students are involved in various aspects of the experiment, including the installation of a simple flow photochemical reactor, reaction monitoring, product purification, and characterization. Through this project, students not only gain insights into photochemical reactions but also cultivate their creativity and research skills in the realm of green and sustainable chemistry. They acquire hands-on experience in thin-layer chromatography, column chromatography, and spectroscopic analysis techniques like IR and NMR, enhancing their practical skills and environmental awareness. This innovative experiment aligns with the principles of green chemistry and miniaturization and is suitable for incorporation into undergraduate laboratory courses such as Organic Chemistry Laboratory and Comprehensive Chemistry Laboratory. Its introduction into laboratory teaching can enrich teaching practices, promote active learning, and elevate the quality of practical education.
-
-
-
[1]
Schultz, D. M.; Yoon, T. P. Science 2014, 343, 985.
-
[2]
-
[3]
Zheng, Y.; Lin, L.; Wang, B.; Wang, X. Angew. Chem. Int. Ed. 2015, 54(44), 12868.
-
[4]
-
[5]
Cai, Y.; Tang, Y.; Fan, L. L.; Lefebvre, Q.; Hou, H.; Rueping, M. ACS Catal. 2018, 8(10), 9471.
-
[6]
Geng, P. X.; Tang, Y. R.; Pan, G. L.; Wang, W. T.; Hu, J. C.; Cai, Y. F. Green Chem. 2019, 21, 6116.
-
[7]
Kaila, N.; Follows, B.; Leung, L,; Thomason, J.; Huang, A.; Moretto, A.; Janz, K.; Lowe, M.; Mansour, T.; Hubeau, C.; et al. J. Med. Chem. 2014, 57(4), 1299.
-
[8]
Sterckx, H.; Morel, B.; Maes, B. U. W. Angew. Chem. Int. Ed. 2019, 58(24), 7946.
-
[9]
-
[1]
-
-
-
[1]
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. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
-
[2]
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
-
[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]
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
-
[5]
Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
-
[6]
Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
-
[7]
Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
-
[8]
Xinzhe HUANG , Lihui XU , Yue YANG , Liming WANG , Zhangyong LIU , Zhongjian WANG . Preparation and visible light responsive photocatalytic properties of BiSbO4/BiOBr. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 284-292. doi: 10.11862/CJIC.20240212
-
[9]
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
-
[10]
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
-
[11]
Qin Li , Huihui Zhang , Huajun Gu , Yuanyuan Cui , Ruihua Gao , Wei-Lin Dai . In situ Growth of Cd0.5Zn0.5S Nanorods on Ti3C2 MXene Nanosheet for Efficient Visible-Light-Driven Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2025, 41(4): 100031-. doi: 10.3866/PKU.WHXB202402016
-
[12]
Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO2 mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
-
[13]
Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
-
[14]
Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO3/SiO2. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
-
[15]
Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
-
[16]
Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
-
[17]
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
-
[18]
Li'na ZHONG , Jingling CHEN , Qinghua ZHAO . Synthesis of multi-responsive carbon quantum dots from green carbon sources for detection of iron ions and L-ascorbic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 709-718. doi: 10.11862/CJIC.20240280
-
[19]
Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
-
[20]
Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
-
[1]
Metrics
- PDF Downloads(1)
- Abstract views(85)
- HTML views(6)