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]
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
-
[2]
Tongyan Yu , Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070
-
[3]
Dan Liu . 可见光-有机小分子协同催化的不对称自由基反应研究进展. University Chemistry, 2025, 40(6): 118-128. doi: 10.12461/PKU.DXHX202408101
-
[4]
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
-
[5]
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
-
[6]
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
-
[7]
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
-
[8]
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
-
[9]
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
-
[10]
Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
-
[11]
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
-
[12]
Zhang Xiaofei , Xu Shanhao , Wang Zhiyuan , He Long , Huang Tangcheng , Xu Yongming , Bian Yucui , Li Yike , Chen Haijun , Li Zhongjun . Surface doping of graphene into BiOCl for efficient photocatalytic amine coupling under visible light. Acta Physico-Chimica Sinica, 2026, 42(5): 100202-. doi: 10.1016/j.actphy.2025.100202
-
[13]
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
-
[14]
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
-
[15]
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
-
[16]
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
-
[17]
Mengyun Wu , Yuxin Deng , Wenhui Wang , Dongdong Xu , Langui Xie , Peipei Sun . 电化学合成4-氯-2-三异丙基硅基喹啉. University Chemistry, 2026, 41(5): 222-229. doi: 10.12461/PKU.DXHX202511044
-
[18]
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
-
[19]
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): 100031-0. doi: 10.3866/PKU.WHXB202402016
-
[20]
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
-
[1]
Metrics
- PDF Downloads(5)
- Abstract views(734)
- HTML views(68)
Login In
DownLoad: