Citation: Tingting Yu, Si Chen, Lianglong Sun, Tongtong Shi, Kai Sun, Xin Wang. Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles[J]. University Chemistry, ;2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022 shu

Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles

School of Pharmacy, Yantai University, Yantai 264005, Shandong Province, China

Received Date: 8 January 2024
Revised Date: 19 February 2024

Photochemical synthesis technology has gained attention in the field of synthetic chemistry due to its mild reaction conditions, simple equipment, and utilization of light energy. However, photochemical synthesis experiments are rarely incorporated into undergraduate organic chemistry laboratory courses. Fluorine-containing nitrogen heterocycles are widely present in natural products and bioactive molecules, serving as important intermediates in organic synthesis. Based on our team’s recent research achievements, a comprehensive experiment for the photochemical synthesis of difluoropyrroles has been designed. This experiment encompasses the preparation of substrates and products, structural characterization, and analysis of photochemical synthesis. It aims to enhance students’ skills in organic synthesis and structural analysis, while also sparking their interest in organic chemistry experiments. Furthermore, it plays a significant role in cultivating students’ innovative consciousness and promoting the concept of “green synthesis” by incorporating scientific research outcomes into organic chemistry laboratory teaching.
- Photochemical synthesis,
- Difluoropyrroles,
- Nitrogen heterocycle,
- Green chemistry
1. [1]
  Jitender, S.; Shivani, S.; Anuj, S. J. Org. Chem. 2021, 86 (1), 24.
2. [2]
  Hou, H. L.; Zeng, X. K.; Zhang, X. W. Angew. Chem. Int. Ed. 2020, 59 (40), 17356.
3. [3]
  Zhang, Y.; Qiu, G.; Liu, F.; Zhao, D.; Tian, M.; Sun, K. Molecules 2023, 28, 3137.
4. [4]
  Zhang, Z.; Tan, P. P.; Wang, S. L.; Wang, H. C.; Han, L. L.; Yang, S. B.; Sun, K. Org. Lett. 2023, 25, 4208.
5. [5]
  Abusallout, I.; Hua, G. H. Chemosphere 2022, 308, 136206.
6. [6]
  Yu, W. L.; Ren, Z. G.; Ma, W.; Zheng, H. X.; Wu, W. S.; Xu, P. F. Green Chem. 2022, 24, 6131.
7. [7]
  Zhang, C.; Wang, Y.; Song, Y. G.; Gao, H. Y.; Sun, Y. H.; Sun, X. Y.; Yang, Z.; Zhan, L. P.; Yu, Z. X.; Rao, Y. CCS Chem. 2019, 1 (4), 352.
8. [8]
  Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.
9. [9]
10. [10]
  Yang, S. H.; Song, J. C.; Yang, H.; Zhou, M. Y.; Wei, Z. H.; Gao, J. H.; Dong, D. Q.; Wang, Z. L. Chin. Chem. Lett. 2023, 34, 108131.
11. [11]
  Ye, Z. P.; Hu, Y. Z.; Guan, J. P.; Chen, K.; Liu, F.; Gao, J.; Xiao, J. A.; Xiang, H. Y.; Chen, X. Q.; Yang, H. Org. Lett. 2021, 23, 4754.
12. [12]
  Muhammad, Q.; Kazuhiro, T. Chem. Mater. 2017, 29 (1), 158.
13. [13]
  Braslavsky, S. E.; Braun, A. M.; Cassano, A. E.; Emeline, A. V.; Litter, M. I.; Palmisano, L.; Parmon, V. N.; Serpone, N. Pure Appl. Chem. 2011, 83, 931.
14. [14]
  Chen, Z.; Jaramillo, T. F.; Deutsch, T. G.; Kleiman-Shwarsctein, A.; Forman, A. Mater. Res. 2010, 25, 3.
1. [1]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
2. [2]
  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
3. [3]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
4. [4]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
5. [5]
  Zijian Zhao , Yanxin Shi , Shicheng Li , Wenhong Ruan , Fang Zhu , Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094
6. [6]
  Jihua Deng , Xinshi Wu , Dichang Zhong . Exploration of Green Teaching and Ideological and Political Education in Chemical Experiment of “Preparation of Ammonium Ferrous Sulfate”. University Chemistry, 2024, 39(10): 325-329. doi: 10.12461/PKU.DXHX202405046
7. [7]
  Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
8. [8]
  Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO₂制C₂₊产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
9. [9]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
10. [10]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
11. [11]
  Zhilian Liu , Wengui Wang , Hongxiao Yang , Yu Cui , Shoufeng Wang . Ideological and Political Education Design for the Synthesis of Irinotecan Drug Intermediate 7-Ethyl Camptothecin. University Chemistry, 2024, 39(2): 89-93. doi: 10.3866/PKU.DXHX202306012
12. [12]
  Yunchao Li , Shanying Chen , Ke Qi , Kangning Huo , Shuxin Li , Jingyi Li , Ying Wei , Louzhen Fan . A New Colloid Electrophoresis Experiment Incorporating Characteristics of Inquiry Learning and Ideological and Political Education. University Chemistry, 2024, 39(2): 47-51. doi: 10.3866/PKU.DXHX202308063
13. [13]
  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
14. [14]
  Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C₆₀-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
15. [15]
  Yiming Lu , Xiang Xie , Xiaoqing Qiu , Yang Liu , Xinyuan Cheng . The New Year’s Eve of the Aviation Brake Material Family. University Chemistry, 2024, 39(9): 203-207. doi: 10.12461/PKU.DXHX202403061
16. [16]
  Ruiyuan Xu , Yuxin Wang , Yuru Zhang , Wanmei Li . Who Destroyed Snowflake Castle. University Chemistry, 2024, 39(9): 224-228. doi: 10.12461/PKU.DXHX202311056
17. [17]
  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
18. [18]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
19. [19]
  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
20. [20]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(378)
HTML views(44)

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