Citation: Geyang Song, Dong Xue, Gang Li. Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides[J]. University Chemistry, ;2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030 shu

Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides

Geyang Song ^1,2 ,
Dong Xue ^1,2 ,
Gang Li ^1,2,,

1.
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, Xi'an 710119, China;
2.
School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, China

Corresponding author: Gang Li, gangli@snnu.edu.cn
Received Date: 7 August 2023

Aniline compounds are important organic intermediates and basic chemical raw materials, widely applied in research fields such as pharmaceuticals, agrochemicals, dyes, and functional materials. The development of efficient and versatile synthesis of aniline derivatives is one of the research hotspots that have been attracting much attention. In the past few decades, the study of transition metal-catalyzed synthesis of aniline derivatives from aryl halides has attracted significant attention from chemists due to its advantages of broad substrate applicability, good functional group compatibility, and high reaction selectivity. This review summarizes the research progress in transition metal-catalyzed synthesis of aniline derivatives from aryl halides, including: (1) palladium-catalyzed synthesis of aniline derivatives from aryl halides; (2) copper-catalyzed synthesis of aniline derivatives from aryl halides; (3) nickel-catalyzed synthesis of aniline derivatives from aryl halides.
- Transition metal-catalyzed,
- Anilines,
- Aryl halide,
- Amination reaction
1. [1]
  (b) Lawrence, S. A. Amines: Synthesis, Properties and Applications; Cambridge University Press: Cambridge, UK, 2004; p. 450.
2. [2]
  (a) Weissermel, K.; Arpe, H.-J. Industrial Organic Chemistry; Wiley-VCH Verlag GmbH: Weinheim, Germany, 2008; pp. I–XIX.
3. [3]
  Schranck, J.; Tlili, A. ACS Catal. 2018, 8, 405.
4. [4]
  (b) Ruiz-Castillo, P.; Buchwald, S. L. Chem. Rev. 2016, 116, 12564.
5. [5]
  (a) Bariwal, J.; Van der Eycken, E. V. Chem. Soc. Rev. 2013, 42, 9283.
6. [6]
  (c) Forero-Cortés, P. A.; Haydl, A. M. Org. Process Res. Dev. 2019, 23, 1478.
7. [7]
  Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 10028.
8. [8]
  (b) Sambiagio, C.; Marsden, S. P.; Blacker, A. J.; McGowan, P. C. Chem. Soc. Rev. 2014, 43, 3525.
9. [9]
  Vo, G. D; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 11049.
10. [10]
11. [11]
  (d) Cai, Q.; Zhou, W. Chin. J. Chem. 2020, 38, 879.
12. [12]
  Green, R. A.; Hartwig, J. F. Org. Lett. 2014, 16, 4388.
13. [13]
  (e) Yang, Q.; Zhao, Y.; Ma, D. Org. Process Res. Dev. 2022, 26, 1690.
14. [14]
  Klinkenberg, J. L.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 11830.
15. [15]
  (b) Gao, J.; Bhunia, S.; Wang, K.; Gan, L.; Xia, S.; Ma, D. Org. Lett. 2017, 19, 2809.
16. [16]
  Surry, D. S.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 10354.
17. [17]
  (b) Twilton, J.; Le, C.; Zhang, P.; Shaw, M. H.; Evans R. W.; MacMillan, D. W. C. Nat. Rev. Chem. 2017, 1, 0052.
18. [18]
  Cheung, C. W.; Surry, D. S.; Buchwald, S. L. Org. Lett. 2013, 15, 3734.
19. [19]
  Schulz, T.; Torborg, C.; Enthaler, S.; Schäffner, B.; Dumrath, A.; Spannenberg, A.; Neumann, H.; Börner, A.; Beller, M. Chem. Eur. J. 2009, 15, 4528.
20. [20]
  (c) Chan, A. Y.; Perry, I. B.; Bissonnette, N. B.; Buksh, B. F.; Edwards, G. A.; Frye, L. I.; Garry, O. L.; Lavagnino, M. N.; Li, B. X.; Liang, Y.; et al. Chem. Rev. 2022, 122, 1485.
21. [21]
  (b) Song, G.; Yang, L.; Li, J.-S.; Tang, W.-J.; Zhang, W.; Cao, R.; Wang, C.; Xiao, J.; Xue, D. Angew. Chem. Int. Ed, 2021, 60, 21536.
22. [22]
  Dumrath, A.; Lübbe, C.; Neumann, H.; Jackstell, R.; Beller, M. Chem. Eur. J. 2011, 17, 9599.
23. [23]
  (c) Song, G.; Nong, D.-Z.; Li, J.-S.; Li, G.; Zhang, W.; Cao, R.; Wang, C.; Xiao, J.; Xue, D. J. Org. Chem. 2022, 87, 10285.
24. [24]
  Lundgren, R. J.; Sappong-Kumankumah, A.; Stradiotto, M. Chem. Eur. J. 2010, 16, 1983.
25. [25]
  Lundgren, R. J.; Peters, B. D.; Alsabeh, P. G.; Stradiotto, M. Angew. Chem. Int. Ed. 2010, 49, 4071.
26. [26]
  (d) Song, G.; Li, Q.; Nong, D.-Z.; Song, J.; Li, G.; Wang, C.; Xiao, J.; Xue, D. Chem. Eur. J. 2023, 29, e202300458.
27. [27]
  Alsabeh, P. G.; Lundgren, R. J.; McDonald, R.; Johansson Seechurn, C. C. C.; Colacot, T. J.; Stradiotto, M. Chem. Eur. J. 2013, 19, 2131.
28. [28]
  Lombardi, C.; Day, J.; Chandrasoma, N.; Mitchell, D.; Rodriguez, M. J.; Farmer, J. L.; Organ, M. G. Organometallics 2017, 36, 251.
29. [29]
  Lindley, J. Tetrahedron 1984, 40, 1433.
30. [30]
  (a) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054.
31. [31]
  Lang, F.; Zewge, D.; Houpis, I. N.; Volante, R. P. Tetrahedron Lett. 2001, 42, 3251.
32. [32]
  Kim, J.; Chang, S. Chem. Commun. 2008, 3052.
33. [33]
  Xia, N.; Taillefer, M. Angew. Chem. Int. Ed. 2009, 48, 337.
34. [34]
  Jiang, L.; Lu, X.; Zhang, H.; Jiang, Y.; Ma, D. J. Org. Chem. 2009, 74, 4542.
35. [35]
  (a) Fan, M.; Zhou, W.; Jiang, Y.; Ma, D. Org. Lett. 2015, 17, 5934.
36. [36]
  Wang, D.; Cai, Q.; Ding, K. Adv. Synth. Catal. 2009, 351, 1722.
37. [37]
  Meng, F.; Zhu, X.; Li, Y.; Xie, J.; Wang, B.; Yao, J.; Wan, Y. Eur. J. Org. Chem. 2010, 6149.
38. [38]
  Elmkaddem, M. K.; Fischmeister, C.; Thomas, C. M.; Renaud, J.-L. Chem. Commun. 2010, 46, 925.
39. [39]
  Zeng, X.; Huang, W.; Qiu, Y.; Jiang, S. Org. Biomol. Chem. 2011, 9, 8224.
40. [40]
  Quan, Z.; Xia, H.; Zhang, Z.; Da, Y.; Wang, X. Chin. J. Chem. 2013, 31, 501.
41. [41]
  Wu, Z.; Jiang, Z.; Wu, D.; Xiang, H.; Zhou, X. Eur. J. Org. Chem. 2010, 1854.
42. [42]
  Xu, H.; Wolf, C. Chem. Commun. 2009, 3035.
43. [43]
  Wu, X.-F.; Darcel, C. Eur. J. Org. Chem. 2009, 4753.
44. [44]
  Fantasia, S.; Windisch, J.; Scalone, M. Adv. Synth. Catal. 2013, 355, 627.
45. [45]
  Borzenko, A.; Rotta-Loria, N. L.; MacQueen, P. M.; Lavoie, C. M.; McDonald, R.; Stradiotto, M. Angew. Chem. Int. Ed. 2015, 54, 3773.
46. [46]
  Green R. A.; Hartwig, J. F. Angew. Chem. Int. Ed. 2015, 54, 3768.
47. [47]
  Lavoie, C. M.; MacQueen, P. M.; Rotta-Loria, N. L.; Sawatzky, R. S.; Borzenko, A.; Chisholm, A J.; Hargreaves, B. K.V.; McDonald, R.; Ferguson, M. J.; Stradiotto, M. Nat. Commun. 2016, 7, 11073.
48. [48]
  (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
49. [49]
  (a) Li, G.; Yang, L.; Liu, J.-J.; Zhang, W.; Cao, R.; Wang, C.; Zhang, Z.; Xiao, J.; Xue, D. Angew. Chem. Int. Ed, 2021,60, 5230.
50. [50]
  Song, G.; Nong, D.-Z.; Li, Q.; Yan, Y.; Li, G.; Fan, J.; Zhang, W.; Cao, R.; Wang, C.; Xiao, J.; et al. ACS Catal. 2022, 12, 15590.
1. [1]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
2. [2]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
3. [3]
  Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
4. [4]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
5. [5]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
6. [6]
  Qi Zhang , Ziyu Liu , Hongxia Tan , Jun Tong , Dazhen Xu . Research Progress on Direct Synthesis of β-Hydroxy Sulfones via Difunctionalization of Olefins. University Chemistry, 2025, 40(11): 199-209. doi: 10.12461/PKU.DXHX202412064
7. [7]
  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
8. [8]
  Bolin Sun , Jie Chen , Ling Zhou . 乙烯型卤代烃的亲核取代反应. University Chemistry, 2025, 40(8): 152-157. doi: 10.12461/PKU.DXHX202410032
9. [9]
  Hanxue LIU , Shijie LI , Meng REN , Xuling XUE , Hongke LIU . Design and antitumor properties of dehydroabietic acid functionalized cyclometalated iridium(Ⅲ) complex. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1483-1494. doi: 10.11862/CJIC.20250031
10. [10]
  Xinwan Zhao , Yue Cao , Minjun Lei , Zhiliang Jin , Tsubaki Noritatsu . Constructing S-scheme heterojunctions by integrating covalent organic frameworks with transition metal sulfides for efficient noble-metal-free photocatalytic hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(12): 100152-0. doi: 10.1016/j.actphy.2025.100152
11. [11]
  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
12. [12]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-0. doi: 10.3866/PKU.WHXB202407005
13. [13]
  Yan Kong , Wei Wei , Lekai Xu , Chen 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
14. [14]
  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
15. [15]
  Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
16. [16]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . Effect of Interlayer Anions in Layered Double Hydroxides on the Photothermocatalytic CO₂ Methanation of Derived Ni-Al₂O₃ Catalysts. Acta Physico-Chimica Sinica, 2025, 41(1): 100002-0. doi: 10.3866/PKU.WHXB202309002
17. [17]
  Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
18. [18]
  Ruizhi Duan , Xiaomei Wang , Panwang Zhou , Yang Liu , Can Li . The role of hydroxyl species in the alkaline hydrogen evolution reaction over transition metal surfaces. Acta Physico-Chimica Sinica, 2025, 41(9): 100111-0. doi: 10.1016/j.actphy.2025.100111
19. [19]
  Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(552)
HTML views(66)

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