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
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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.
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Keywords:
- Friedel-Crafts alkylation,
- Organic synthesis,
- Catalysis
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[1]
Friedel, C.; Crafts, J. M. Bull. Soc. Chim. Fr. 1877, 27, 530.
-
[2]
Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem. Int. Ed. 2009, 48, 3817.
-
[3]
Mo, X.; Yakiwchuk, J.; Dansereau, J.; McCubbin, J. A.; Hall, D. G. J. Am. Chem. Soc. 2015, 137, 9694.
-
[4]
Niggemann, M.; Meel, M. J. Angew. Chem. Int. Ed. 2010, 49, 3684.
-
[5]
Jiao, Z.; Lim, L. H.; Hirao, H.; Zhou, J. S. Angew. Chem. Int. Ed. 2018, 57, 6294.
-
[6]
He, T.; Klare, H. F. T.; Oestreich, M. ACS Catal. 2021, 11, 12186.
-
[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]
Sheng, Y.-F.; Gu, Q.; Zhang, A.-J.; You, S.-L. J. Org. Chem. 2009, 74, 6899.
-
[9]
Herrera, R. P.; Sgarzan, V.; Bernardi, L.; Ricci, A. Angew. Chem. Int. Ed. 2005, 44, 6576.
-
[10]
Li, Q.-Y.; Cheng, S.; Ye, Z.; Huang, T.; Yang, F.; Lin, Y.-M.; Gong, L. Nat. Commun. 2023, 14, 6366.
-
[11]
Lutovsky, G. A.; Gockel, S. N.; Bundesmann, M. W.; Bagley, S. W.; Yoon, T. P. Chem 2023, 9, 1610.
-
[12]
Pan, X.; Wang, W.; Gao, X.; Hao, G.; Li, T. Chem. Eur. J. 2023, 29, e202203876.
-
[13]
Tengg, M.; Stecher, H.; Offner, L.; Plasch, K.; Anderl, F.; Weber, H.; Schwab, H.; Gruber-Khadjawi, M. ChemCatChem 2016, 8, 1354.
-
[14]
Schultz, E. E.; Braffman, N. R.; Luescher, M. U.; Hager, H. H.; Balskus, E. P. Angew. Chem. Int. Ed. 2019, 58, 3151.
-
[15]
Henche, S.; Nestl, B. M.; Hauer, B. ChemCatChem 2021, 13, 3405.
-
[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.
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