Citation: Zhenyu Guo, Yuhang Li, Shuai Chen, Chengjian Zhu, Jin Xie. Photoredox/Nickel-Catalyzed Synthesis of 4'-Methoxypropiophenone[J]. University Chemistry, ;2024, 39(1): 210-217. doi: 10.3866/PKU.DXHX202306046 shu

Photoredox/Nickel-Catalyzed Synthesis of 4'-Methoxypropiophenone

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China

Corresponding author: Jin Xie, xie@nju.edu.cn
Received Date: 23 June 2023

The photo-nickel synergistic catalytic reaction emerges as a promising synthetic method, offering advantages such as high yields, mild reaction conditions, and broad scope. Guided by the principles of sustainable development, we have successfully synthesized valued aromatic ketone derivatives utilizing prevalent industrial feedstocks, aromatic carboxylic acids and ethylene under mild reaction conditions. It would be the first example of photo-nickel synergistic catalyzed reaction between aromatic acids and ethylene under air atmosphere. This synthetic method features in a high efficiency utilization of resource, simple operation and easy access for the students to grasp. This approach not only bridges a knowledge gap in teaching photochemical reactions within foundational organic chemistry experiments but also holds substantial practical and pedagogical merit.
- Visible-light photocatalysis,
- nickel catalysis,
- Aryl ketones,
- Organic chemistry experiment
1. [1]
  Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.
2. [2]
  Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437.
3. [3]
  Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433.
4. [4]
  Zhang, M.; Yuan, X.-A.; Zhu, C.; Xie, J. Angew. Chem. Int. Ed. 2019, 58, 312.
5. [5]
  Robbert, K.; Kleerebezem, R.; Beckers, J.; Pol, L. W. H.; Lettinga, G. Biotechnol. Bioeng. 2005, 91, 169.
6. [6]
7. [7]
  Zhang, L.; Chen, S.; He, H.; Li, W.; Zhu, C.; Xie, J. Chem. Commun. 2021, 57, 9064.
8. [8]
9. [9]
  Tran, V. T.; Li, Z. Q.; Apolinar, O.; Derosa, J.; Joannou, M. V.; Wisniewski, S. R.; Eastgate, M. D.; Engle, K. M. Angew. Chem. Int. Ed. 2020, 59, 7409.
1. [1]
  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
2. [2]
  Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
3. [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. [4]
  Ying Xiong , Guangao Yu , Lin Wu , Qingwen Liu , Houjin Li , Shuanglian Cai , Zhanxiang Liu , Xingwen Sun , Yuan Zheng , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Determination of Physical Constants of Organic Compounds. University Chemistry, 2025, 40(5): 106-121. doi: 10.12461/PKU.DXHX202503079
5. [5]
  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
6. [6]
  Houjin Li , Wenjian Lan . Name Reactions in University Organic Chemistry Laboratory. University Chemistry, 2024, 39(4): 268-279. doi: 10.3866/PKU.DXHX202310016
7. [7]
  Zhanxiang Liu , Chengshan Yuan , Jie Han , Shuanglian Cai , Qihan Zhang , Lin Wu , Yuan Zheng , Xingwen Sun , Qingwen Liu , Ying Xiong , Guangao Yu , Xin Du , Houjin Li , Jianrong Zhang , Shuyong Zhang . Recommendations for Basic Operations and Standards for Organic Chemical Extraction and Washing Experiments. University Chemistry, 2025, 40(5): 55-65. doi: 10.12461/PKU.DXHX202410039
8. [8]
  Xuewei Qian , Xingwen Sun , Houjin Li , Zhanxiang Liu , Yuan Zheng , Lin Wu , Shuanglian Cai , Ying Xiong , Guangao Yu , Qingwen Liu , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Shuyong Zhang , Jianrong Zhang . Basic Operations and Specification Suggestions for Organic Chemical Recrystallization Experiments. University Chemistry, 2025, 40(5): 66-75. doi: 10.12461/PKU.DXHX202503126
9. [9]
  Houjin Li , Lin Wu , Xingwen Sun , Yuan Zheng , Zhanxiang Liu , Shuanglian Cai , Ying Xiong , Guangao Yu , Qingwen Liu , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Organic Chemical Chromatography Experiments. University Chemistry, 2025, 40(5): 93-105. doi: 10.12461/PKU.DXHX202408100
10. [10]
  Chengshan Yuan , Xiaolong Li , Xiuping Yang , Xiangfeng Shao , Zitong Liu , Xiaolei Wang , Yongwen Shen . Standardized Operational Guidelines for Mixed-Solvent Recrystallization in Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 122-127. doi: 10.12461/PKU.DXHX202504073
11. [11]
  Yi-Lin Xie , Jian-Ji Zhong , Qing-Xiao Tong , Jing-Xin Jian . Exploring “Magic Teaching” as a Means to Integrate Organic Chemistry Experiments with the “Industry-University-Research” Model. University Chemistry, 2025, 40(5): 252-260. doi: 10.12461/PKU.DXHX202407024
12. [12]
  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
13. [13]
  Mengchen Liao , Hua Yang , Younian Liu , Zhen He , Maolin Zhang , Qing Liu , Jiwen Ding . Exploration and Implementation of Refined Management Practices in Basic Organic Chemistry Laboratories. University Chemistry, 2024, 39(10): 164-173. doi: 10.3866/PKU.DXHX202403041
14. [14]
  Gang Liu , Heng Zhang , Ying Ma , Shiling Yuan , Qisheng Song , Zhenghu Xu , Jichao Sun . Exploration and Practice on Improving the Teaching Quality of Organic Chemistry Laboratory Course. University Chemistry, 2024, 39(4): 70-74. doi: 10.3866/PKU.DXHX202309079
15. [15]
  Houjin Li , Shuanglian Cai , Yuan Zheng , Zhanxiang Liu , Chengshan Yuan , Lin Wu , Guangao Yu , Jie Han , Qingwen Liu , Xin Du , Ying Xiong , Qihan Zhang , Xingwen Sun , Jianrong Zhang , Shuyong Zhang . Basic Operations and Standardization Suggestions for Organic Chemistry Distillation Experiments. University Chemistry, 2025, 40(5): 40-54. doi: 10.12461/PKU.DXHX202411053
16. [16]
  Chengshan Yuan , Zhanxiang Liu , Xin Du , Jie Han , Yuan Zheng , Ying Xiong , Qingwen Liu , Guangao Yu , Lin Wu , Shuanglian Cai , Xingwen Sun , Qihan Zhang , Houjin Li , Jianrong Zhang , Shuyong Zhang . Standardized Operational Guidelines for Sublimation in Organic Chemistry Experiments. University Chemistry, 2025, 40(5): 76-83. doi: 10.12461/PKU.DXHX202504015
17. [17]
  Yuan Zheng , Houjin Li , Zhanxiang Liu , Lin Wu , Shuanglian Cai , Ying Xiong , Guangao Yu , Xingwen Sun , Qingwen Liu , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Standardization Suggestions for Organic Chemistry Reflux Experiments. University Chemistry, 2025, 40(5): 84-92. doi: 10.12461/PKU.DXHX202411045
18. [18]
  Huicheng Yang , Qianhong Sun . Practice of Ideological and Political Education in Organic Chemistry Laboratory Courses under the OBE Framework: A Case Study of Berberine Extraction. University Chemistry, 2025, 40(5): 276-282. doi: 10.12461/PKU.DXHX202410091
19. [19]
  Houjin Li , Zhanxiang Liu , Yuan Zheng , Shuanglian Cai , Jie Han , Ying Xiong , Xingwen Sun , Chengshan Yuan , Guangao Yu , Qingwen Liu , Lin Wu , Qihan Zhang , Xin Du , Jianrong Zhang , Shuyong Zhang . Exploration and Practice of the Construction of the Basic Operation Standard of Organic Chemistry Experiment Based in Virtual Teaching Research. University Chemistry, 2025, 40(5): 230-237. doi: 10.12461/PKU.DXHX202502064
20. [20]
  Jian Jin , Jing Cheng , Xueping Yang . Integration Practice of Organic Chemistry Experiment and Safety Education: Taking the Synthesis of Triphenylmethanol as an Example. University Chemistry, 2024, 39(3): 345-350. doi: 10.3866/PKU.DXHX202309010

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1019)
HTML views(64)

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