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

  • 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.
  • 加载中
    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.

  • 加载中
    1. [1]

      Fengxiao Wang Zhiwei Miao Yaofeng Yuan . 有机磷化学与化学教学. University Chemistry, 2025, 40(8): 158-168. doi: 10.12461/PKU.DXHX202410077

    2. [2]

      Yongjian Zhang Fangling Gao Hong Yan Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035

    3. [3]

      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

    4. [4]

      Ran YuChen HuRuili GuoRuonan LiuLixing XiaCenyu YangJianglan Shui . Catalytic Effect of H3PW12O40 on Hydrogen Storage of MgH2. Acta Physico-Chimica Sinica, 2025, 41(1): 100001-0. doi: 10.3866/PKU.WHXB202308032

    5. [5]

      Xiaogang Liu Mengyu Chen Yanyan Li Xiantao Ma . Experimental Reform in Applied Chemistry for Cultivating Innovative Competence: A Case Study of Catalytic Hydrogen Production from Liquid Formaldehyde Reforming at Room Temperature. University Chemistry, 2025, 40(7): 300-307. doi: 10.12461/PKU.DXHX202408007

    6. [6]

      Shuhui Li Rongxiuyuan Huang Yingming Pan . Electrochemical Synthesis of 2,5-Diphenyl-1,3,4-Oxadiazole: A Recommended Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(5): 357-365. doi: 10.12461/PKU.DXHX202407028

    7. [7]

      Lewang YuanYaoyao PengZong-Jie GuanYu Fang . Insights into the development of 2D covalent organic frameworks as photocatalysts in organic synthesis. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-0. doi: 10.1016/j.actphy.2025.100086

    8. [8]

      Wenjie SHIFan LUMengwei CHENJin WANGYingfeng 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

    9. [9]

      Zelong LIANGShijia QINPengfei GUOHang XUBin 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

    10. [10]

      Yan KongWei WeiLekai XuChen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO2 Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049

    11. [11]

      Xuejie WangGuoqing CuiCongkai WangYang YangGuiyuan JiangChunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044

    12. [12]

      Jiajie Li Xiaocong Ma Jufang Zheng Qiang Wan Xiaoshun Zhou Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117

    13. [13]

      Wenxiu YangJinfeng ZhangQuanlong XuYun YangLijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-0. doi: 10.3866/PKU.WHXB202312014

    14. [14]

      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): -.

    15. [15]

      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

    16. [16]

      Xinxin YUYongxing LIUXiaohong YIMiao CHANGFei WANGPeng WANGChongchen WANG . Photocatalytic peroxydisulfate activation for degrading organic pollutants over the zero-valent iron recovered from subway tunnels. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 864-876. doi: 10.11862/CJIC.20240438

    17. [17]

      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

    18. [18]

      Jingping LiSuding YanJiaxi WuQiang ChengKai Wang . Improving hydrogen peroxide photosynthesis over inorganic/organic S-scheme photocatalyst with LiFePO4. Acta Physico-Chimica Sinica, 2025, 41(9): 100104-0. doi: 10.1016/j.actphy.2025.100104

    19. [19]

      Bizhu ShaoHuijun DongYunnan GongJianhua MeiFengshi CaiJinbiao LiuDichang ZhongTongbu Lu . Metal-Organic Framework-Derived Nickel Nanoparticles for Efficient CO2 Electroreduction in Wide Potential Windows. Acta Physico-Chimica Sinica, 2024, 40(4): 2305026-0. doi: 10.3866/PKU.WHXB202305026

    20. [20]

      Shuang CaoBo ZhongChuanbiao BieBei ChengFeiyan Xu . Insights into Photocatalytic Mechanism of H2 Production Integrated with Organic Transformation over WO3/Zn0.5Cd0.5S S-Scheme Heterojunction. Acta Physico-Chimica Sinica, 2024, 40(5): 2307016-0. doi: 10.3866/PKU.WHXB202307016

Metrics
  • PDF Downloads(44)
  • Abstract views(1408)
  • HTML views(620)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return