Citation: Shiyan Cheng, Yonghong Ruan, Lei Gong, Yumei Lin. Research Advances in Friedel-Crafts Alkylation Reaction[J]. University Chemistry, ;2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024 shu

Research Advances in Friedel-Crafts Alkylation Reaction

College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, China

Received Date: 5 March 2024
Revised Date: 20 May 2024

The Friedel-Crafts alkylation reaction represents a pivotal organic transformation for the formation of carbon-carbon bonds, holding extensive applications within the realms of both organic synthesis and pharmaceutical chemistry. This article presents a comprehensive review of the mechanism underlying the Friedel-Crafts alkylation reaction, alongside recent advancements in various catalytic approaches, such as metal catalysis, organocatalysis, visible light photocatalysis, enzymatic and electrochemical catalysis. By merging cutting-edge scientific developments with undergraduate teaching content, this review endeavors to inspire students’ learning interests while fostering their capacity for innovative thinking.
- Friedel-Crafts alkylation,
- Organic synthesis,
- Catalysis
1. [1]
  Friedel, C.; Crafts, J. M. Bull. Soc. Chim. Fr. 1877, 27, 530.
2. [2]
  Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem. Int. Ed. 2009, 48, 3817.
3. [3]
  Mo, X.; Yakiwchuk, J.; Dansereau, J.; McCubbin, J. A.; Hall, D. G. J. Am. Chem. Soc. 2015, 137, 9694.
4. [4]
  Niggemann, M.; Meel, M. J. Angew. Chem. Int. Ed. 2010, 49, 3684.
5. [5]
  Jiao, Z.; Lim, L. H.; Hirao, H.; Zhou, J. S. Angew. Chem. Int. Ed. 2018, 57, 6294.
6. [6]
  He, T.; Klare, H. F. T.; Oestreich, M. ACS Catal. 2021, 11, 12186.
7. [7]
  Zhang, S.; Vayer, M.; Noël, F.; Vuković, V. D.; Golushko, A.; Rezajooei, N.; Rowley, C. N.; Lebœuf, D.; Moran, J. Chem 2021, 7, 3425.
8. [8]
  Sheng, Y.-F.; Gu, Q.; Zhang, A.-J.; You, S.-L. J. Org. Chem. 2009, 74, 6899.
9. [9]
  Herrera, R. P.; Sgarzan, V.; Bernardi, L.; Ricci, A. Angew. Chem. Int. Ed. 2005, 44, 6576.
10. [10]
  Li, Q.-Y.; Cheng, S.; Ye, Z.; Huang, T.; Yang, F.; Lin, Y.-M.; Gong, L. Nat. Commun. 2023, 14, 6366.
11. [11]
  Lutovsky, G. A.; Gockel, S. N.; Bundesmann, M. W.; Bagley, S. W.; Yoon, T. P. Chem 2023, 9, 1610.
12. [12]
  Pan, X.; Wang, W.; Gao, X.; Hao, G.; Li, T. Chem. Eur. J. 2023, 29, e202203876.
13. [13]
  Tengg, M.; Stecher, H.; Offner, L.; Plasch, K.; Anderl, F.; Weber, H.; Schwab, H.; Gruber-Khadjawi, M. ChemCatChem 2016, 8, 1354.
14. [14]
  Schultz, E. E.; Braffman, N. R.; Luescher, M. U.; Hager, H. H.; Balskus, E. P. Angew. Chem. Int. Ed. 2019, 58, 3151.
15. [15]
  Henche, S.; Nestl, B. M.; Hauer, B. ChemCatChem 2021, 13, 3405.
16. [16]
  Lunghi, E.; Ronco, P.; Negra, F. D.; Trucchi, B.; Verzini, M.; Merli, D.; Casali, E.; Kappe, C. O.; Cantillo, D.; Zanoni, G. J. Org. Chem. 2023, 88, 16783.
1. [1]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
2. [2]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . 杂多酸H₃PW₁₂O₄₀高效催化MgH₂储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032
3. [3]
  Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO₂ reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
4. [4]
  Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360
5. [5]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
6. [6]
  .
  CCS Chemistry 综述推荐│绿色氧化新思路：光/电催化助力有机物高效升级
  . CCS Chemistry, 2025, 7(10.31635/ccschem.024.202405369): -.
7. [7]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
8. [8]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
9. [9]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
10. [10]
  Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
11. [11]
  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
12. [12]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
13. [13]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
14. [14]
  Jiaojiao Yu , Bo Sun , Na Li , Cong Wen , Wei Li . Improvement of Classical Organic Experiment Based on the “Reverse-Step Optimization Method”: Taking Synthesis of Ethyl Acetate as an Example. University Chemistry, 2025, 40(3): 333-341. doi: 10.12461/PKU.DXHX202405177
15. [15]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
16. [16]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
17. [17]
  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
18. [18]
  Yue Wu , Jun Li , Bo Zhang , Yan Yang , Haibo Li , Xian-Xi Zhang . Research on Kinetic and Thermodynamic Transformations of Organic-Inorganic Hybrid Materials for Fluorescent Anti-Counterfeiting Application information: Introducing a Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(6): 390-399. doi: 10.3866/PKU.DXHX202403028
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]
  Yukun Chang , Haoqin Huang , Baolei Wang . Preparation of Trans-Cinnamic Acid via “One-Pot” Protocol of Aldol Condensation-Hydrolysis Reaction: Recommending an Improved Organic Synthesis Experiment. University Chemistry, 2024, 39(4): 322-328. doi: 10.3866/PKU.DXHX202309095

Get Citation

PDF

XML

Metrics

PDF Downloads(20)
Abstract views(684)
HTML views(381)

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