Citation: Xie Jianwei, Wang Xiaochuang, Wu Fengtian, Zhang Jie. Research Progress in Ligand-Assisted Copper-Catalyzed C-N Cross-Coupling Reaction in Aqueous Media or Pure Water[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3026-3039. doi: 10.6023/cjoc201907051 shu

Research Progress in Ligand-Assisted Copper-Catalyzed C-N Cross-Coupling Reaction in Aqueous Media or Pure Water

a.
College of Chemistry and Bioengineering, Hunan University of Science and Engineering, Yongzhou, Hunan 425199
b.
Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003
c.
Jiangxi Province Key Laboratory of Polymer Micro/Nano Manufacturing and Devices, East China University of Technology, Nanchang 330013

Corresponding author: Xie Jianwei, cesxjw@foxmail.com
Received Date: 29 July 2019
Revised Date: 18 September 2019
Available Online: 9 November 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21606153, 21868032)the National Natural Science Foundation of China 21868032the National Natural Science Foundation of China 21606153

Figures(2)

Copper-catalyzed Ullmann-type C-N coupling reaction is one of the most effective methods to construct the C-N bonds. Water, as green and clean solvent, has been successfully employed in various organic reactions. According to the structure of ligands, the progress of ligand-assisted copper-catalyzed C-N cross-coupling reaction in aqueous media or pure water is summarized comprehensively, and the ligands include diamines, hydrazides, phenanthrolines, carbohydrates, pyridine-N-oxides, quinolines, oximes and salen. In addition, ligand-free copper-catalyzed C-N coupling reactions in aquous media or pure water are also reviewed.
- ligand-assisted,
- copper catalyst,
- aqueous media/pure water,
- C-N cross-coupling
1. [1]
  Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054. doi: 10.1021/cr8002505
2. [2]
  (a) Hartwig, J. F. In Palladium-Catalyzed Amination of Aryl Halides and Related Reactions, Wiley, New York, 2002.
  (b) Jiang, L.; Buchwald, S. L. In Palladium-catalyzed Aromatic carbon-nitrogen Bond Formation in Metal-catalyzed Cross- coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004.
  (c) Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954.
  (d) Beletskaya, I. P.; Cheprakov, A. V. Organometallics 2012, 31, 7753.
3. [3]
  Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
4. [4]
  (a) Ullmann, F.; Bielecki, J. Ber. Dtsch. Chem. Ges. 1901, 34, 2174.
  (b) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
5. [5]
  Wolter, M.; Nordamann, G.; Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 973. doi: 10.1021/ol025548k
6. [6]
  Nordamann, G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 4978 doi: 10.1021/ja034809y
7. [7]
8. [8]
  Poliakoff, M.; Fitzpatrick, J.-M.; Farren, T.-R.; Anastas, P. T. Science 2002, 297, 807. doi: 10.1126/science.297.5582.807
9. [9]
  Li, C.-J.; Chan, T.-H. In Comprehensive Organic Reactions in Aqueous Media, 2nd ed., John Wiley & Sons, New Jersey, 2007.
10. [10]
  Carril, M.; SanMartin, R.; Domínguez, E.; Tellitu, I. Green Chem. 2007, 9, 219. doi: 10.1039/B614218D
11. [11]
  Barbero, N.; Carril, M.; SanMartin, R.; Domínguez, E. Tetrahedron 2008, 64, 7283. doi: 10.1016/j.tet.2008.05.072
12. [12]
  Oshovsky, G. V.; Ouali, A.; Xia, N.; Zablocka, M.; Boeré, R. T.; Duhayon, C.; Taillefer, M.; Majoral, J. P. Organometallics 2008, 27, 5733. doi: 10.1021/om800728m
13. [13]
  Swapna, K.; Murthy, S. N.; Nageswar, Y. V. D. Eur. J. Org. Chem. 2010, 2010, 6678. doi: 10.1002/ejoc.201000964
14. [14]
  Peng, J.; Ye, M.; Zong, C.; Hu, F.; Feng, L.; Wang, X.; Wang, Y.; Chen, C. J. Org. Chem. 2011, 76, 716. doi: 10.1021/jo1021426
15. [15]
  Malakar, C. C.; Baskakova, A.; Conrad, J.; Beifuss, U. Chem.-Eur. J. 2012, 18, 8882. doi: 10.1002/chem.201200583
16. [16]
  Shang, X.; Zhao, S.; Chen, W.; Chen, C.; Qiu, H. Chem.-Eur. J. 2014, 20, 1825. doi: 10.1002/chem.201303712
17. [17]
  Shao, B.; Du, H.; Hao, X.; Lu, R.; Luo, Y.; Zhang, S. Chin. J. Chem. Eng. 2016, 24, 1000. doi: 10.1016/j.cjche.2016.01.010
18. [18]
  Bollenbach, M.; Aquino, P. G. V.; de Araújo-Júnior, J. X.; Bourguignon, J.-J.; Bihel, F.; Salomé, C.; Wagner, P.; Schmitt, M. Chem.- Eur. J. 2017, 23, 13676. doi: 10.1002/chem.201700832
19. [19]
  Ding, X.; Bai, J.; Wang, H.; Zhao, B.; Li, J.; Ren, F. Tetrahedron 2017, 73, 172. doi: 10.1016/j.tet.2016.11.066
20. [20]
  Zhu, X.; Ma, Y.; Su, L.; Song, H.; Chen, G.; Liang, D.; Wan, Y. Synthesis 2006, 3955.
21. [21]
  Zhu, X. H.; Su, L.; Huang, L.; Chen, G.; Wang, J.; Song, H.; Wan, Y. Eur. J. Org. Chem. 2009, 2009, 635. doi: 10.1002/ejic.200801049
22. [22]
  Xie, J. W.; Zhu, X. H.; Huang, M. N.; Chen, W.; Wan, Y. Eur. J. Org. Chem. 2010, 2010, 3219. doi: 10.1002/ejoc.201000361
23. [23]
  Meng, F.; Zhu, X. H.; Li, Y.; Xie, J.; Wang, B.; Yao, J.; Wan, Y. Eur. J. Org. Chem. 2010, 2010, 6149. doi: 10.1002/ejoc.201001150
24. [24]
  Li, Y.; Zhu, X. H.; Meng, F.; Wan, Y. Tetrahedron 2011, 67, 5450. doi: 10.1016/j.tet.2011.05.068
25. [25]
  Huang, M.; Lin, X.; Zhu, X.; Peng, W.; Xie, J.; Wan, Y. Eur. J. Org. Chem. 2011, 2011, 4523. doi: 10.1002/ejoc.201100458
26. [26]
  Kurandina, D. V.; Eliseenkov, E. V.; Khaibulova, T. S.; Petrov, A. A.; Boyarskiy, V. P. Tetrahedron 2015, 71, 7931. doi: 10.1016/j.tet.2015.07.071
27. [27]
  Huang, L.; Yu, R.; Zhu, X.; Wan, Y. Tetrahedron 2013, 69, 8974. doi: 10.1016/j.tet.2013.07.036
28. [28]
  Yang, B.; Mao, Z.; Zhu, X.; Wan, Y. Catal. Commun. 2015, 6, 92.
29. [29]
  Engel-Andreasen, J.; Shimpukade, B.; Ulven, T. Green Chem. 2013, 15, 336. doi: 10.1039/C2GC36589H
30. [30]
  Xu, H.; Luo, C.; Li, Z.; Xiang, H.; Zhou, X. J. Heterocycl. Chem. 2016, 53, 1207. doi: 10.1002/jhet.2385
31. [31]
  Thakur, K. G.; Ganapathy, D.; Sekar, G. Chem. Commun. 2011, 47, 5076. doi: 10.1039/c1cc10568j
32. [32]
  Thakur, K. G.; Srinivas, K. S.; Chiranjeevi, K.; Sekar, G. Green Chem. 2011, 13, 2326. doi: 10.1039/c1gc15469a
33. [33]
  Huang, M.; Wang, L.; Zhu, X.; Mao, Z.; Kuang, D.; Wan, Y. Eur. J. Org. Chem. 2012, 2012, 4897. doi: 10.1002/ejoc.201200787
34. [34]
  Wen, M.; Shen, C.; Wang, L.; Zhang, P.; Jin, J. RSC Adv. 2015, 5, 1522. doi: 10.1039/C4RA11183D
35. [35]
  Ge, X.; Chen, X.; Qian, C.; Zhou, S. RSC Adv. 2016, 6, 29638. doi: 10.1039/C6RA03015G
36. [36]
  Ge, X.; Zhang, S.; Chen, X.; Liu, X.; Qian, C. Green Chem. 2019, 21, 2771. doi: 10.1039/C9GC00964G
37. [37]
  Zhou, G.; Chen, W.; Zhang, S.; Liu, X.; Yang, Z.; Ge, X.; Fan, H.-J. Synlett 2019, 193.
38. [38]
  Liang, L.; Li, Z. K.; Zhou, X. G. Org. Lett. 2009, 11, 3294. doi: 10.1021/ol9010773
39. [39]
  Wang, Y.; Zhang, Y.; Yang, B.; Zhang, A.; Yao, Q. Org. Biomol. Chem. 2015, 13, 4101. doi: 10.1039/C5OB00045A
40. [40]
  Wang, Y.; Ling, J.; Zhang, Y.; Zhang, A.; Yao, Q. Eur. J. Org. Chem. 2015, 2015, 4153.
41. [41]
  Wu, F.-T.; Yan, N.-N.; Liu, P.; Xie, J.-W.; Liu, Y.; Dai, B. Tetrahedron Lett. 2014, 55, 3249. doi: 10.1016/j.tetlet.2014.04.039
42. [42]
  Wang, X.; Meng, F.; Zhang, J.; Xie, J.; Dai, B. Catal. Lett. 2018, 148, 1142. doi: 10.1007/s10562-018-2321-8
43. [43]
  Xie, J.-W.; Yao, Z.-B.; Wang, X.-C.; Zhang, J. Tetrahedron 2019, 75, 3788. doi: 10.1016/j.tet.2019.05.067
44. [44]
  Wang, X.; Zhang, J.; Xie, J. Chem. J. Chin. Univ. 2017, 38, 1178 (in Chinese). doi: 10.7503/cjcu20170157
45. [45]
  Karayannis, N. M.; Pytlewski, L. L.; Mikulski, C. M. Coord. Chem. Rev. 1973, 11, 93. doi: 10.1016/S0010-8545(00)82007-X
46. [46]
  Yan, N.-N.; Wu, F.-T.; Zhang, J.; Wei, Q.-B.; Liu, P.; Xie, J.-W.; Dai, B. Asian J. Org. Chem. 2014, 3, 1159. doi: 10.1002/ajoc.201402136
47. [47]
  Liu, L.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider, P. J. J. Org. Chem. 2005, 70, 10135. doi: 10.1021/jo051640t
48. [48]
  Zhang, J. X.; Yin, H. Q.; Han, S. Q. Chin. J. Org. Chem. 2012, 32, 1429 (in Chinese).
49. [49]
  Li, X.; Yang, D.; Jiang, Y.; Fu, H. Green Chem. 2010, 12, 1097. doi: 10.1039/c002172e
50. [50]
  Wu, X.; Hu, W. Chin. J. Chem. 2011, 29, 2124. doi: 10.1002/cjoc.201180368
51. [51]
  Wang, D.; Zhang, F.; Kuang, D.; Yu, J.; Li, J. Green Chem. 2012, 14, 1268. doi: 10.1039/c2gc35077g
52. [52]
  Wang, D.; Kuang, D.; Zhang, F.; Yang, C.; Zhu, X. Adv. Synth. Catal. 2015, 357, 714. doi: 10.1002/adsc.201400785
53. [53]
  Wang, D.; Zheng, Y.; Yang, M.; Zhang, F.; Mao, F.; Yu, J.; Xia, X. Org. Biomol. Chem. 2017, 15, 8009. doi: 10.1039/C7OB02126G
54. [54]
  Bollenbach, M.; Wagner, P.; Aquino, P. G. V.; Bourguignon, J.-J.; Bihel, F.; Salomé, C.; Schmitt, M. ChemSusChem 2016, 9, 3244. doi: 10.1002/cssc.201600801
55. [55]
  Sharma, K. K.; Mandloi, M.; Rai, N.; Jain, R. RSC Adv. 2016, 6, 96762. doi: 10.1039/C6RA23364C
56. [56]
  Ferlin, F.; Trombettoni, V.; Luciani, L.; Fusi, S.; Piermatti, O.; Santoro, S.; Vaccaro, L. Green Chem. 2018, 20, 1634. doi: 10.1039/C8GC00287H
57. [57]
  Kumar, S. V.; Ma, D. Chin. J. Chem. 2018, 36, 1003. doi: 10.1002/cjoc.201800326
58. [58]
  Zhou, Q.; Du, F.; Chen, Y.; Fu, Y.; Chen, G. Tetrahedron Lett. 2019, 60, 1938. doi: 10.1016/j.tetlet.2019.06.033
59. [59]
  Wang, Y.; Wu, Z.; Wang, L.; Li, Z.; Zhou, X. Chem. Eur. J. 2009, 15, 8971. doi: 10.1002/chem.200901232
60. [60]
  Wu, Z.; Jiang, Z.; Wu, D.; Xiang, H.; Zhou, X. Eur. J. Org. Chem. 2010, 2010, 1854. doi: 10.1002/ejoc.201000060
61. [61]
  Wu, Z.; Zhou, L.; Jiang, Z.; Wu, D.; Li, Z.; Zhou, X. Eur. J. Org. Chem. 2010, 2010, 4971. doi: 10.1002/ejoc.201000840
62. [62]
  Yu, L.; Zhou, X.; Wu, D.; Xiang, H. J. Organomet. Chem. 2012, 705, 75. doi: 10.1016/j.jorganchem.2011.12.030
63. [63]
  Pellón, R. F.; Carrasco, R.; Rodés, L. Synth. Commun. 1993, 23, 1447. doi: 10.1080/00397919308011235
64. [64]
  Röttger, S.; Sjöberg, P. J. R.; Larhed, M. J. Comb. Chem. 2007, 9, 204. doi: 10.1021/cc060150r
65. [65]
  Xu, H.-J.; Zheng, F.-Y.; Liang, Y.-F.; Cai, Z.-Y.; Feng, Y.-S.; Che, D.-Q. Tetrahedron Lett. 2010, 51, 669. doi: 10.1016/j.tetlet.2009.11.104
66. [66]
  Mukhopadhyay, C.; Tapaswi, P. K.; Butcher, R. J. Org. Biomol. Chem. 2010, 8, 4720. doi: 10.1039/c0ob00177e
67. [67]
  Xu, H.-J.; Liang, Y.-F.; Cai, Z.-Y.; Qi, H.-X.; Yang, C.-Y.; Feng, Y.-S. J. Org. Chem. 2011, 76, 2296. doi: 10.1021/jo102506x
68. [68]
  Yong, F.-F.; Teo, Y.-C.; Tay, S.-H.; Tan, B. Y.-H.; Lim, K.-H. Tetrahedron Lett. 2011, 52, 1161. doi: 10.1016/j.tetlet.2011.01.005
69. [69]
  Yong, F.-F.; Teo, Y.-C.; Chua, G.-L.; Lim, G. S.; Lin, Y. Tetrahedron Lett. 2011, 52, 1169. doi: 10.1016/j.tetlet.2011.01.003
70. [70]
  Jiao, J.; Zhang, X.-R.; Chang, N.-H.; Wang, J.; Wei, J.-F.; Shi, X.-Y.; Chen, Z.-G. J. Org. Chem. 2011, 76, 1180. doi: 10.1021/jo102169t
71. [71]
  Jin, M.; Zhao, D.; He, G.; Tong, Y.; Han, S. Chin. J. Catal. 2013, 34, 1651. doi: 10.1016/S1872-2067(12)60623-8
72. [72]
  Tan, B. Y.-H.; Teo, Y.-C.; Seow, A.-H. Eur. J. Org. Chem. 2014, 2014, 1541. doi: 10.1002/ejoc.201301561
73. [73]
  Heidarizadeh, F.; Majdi-nasab, A. Tetrahedron Lett. 2015, 56, 6360. doi: 10.1016/j.tetlet.2015.09.128
74. [74]
  Kumari, S.; Shakoor, S. M. A.; Bajaj, K.; Nanjegowda, S. H.; Mallu, P.; Sakhuja, R. Tetrahedron Lett. 2016, 57, 2732. doi: 10.1016/j.tetlet.2016.05.016
75. [75]
  Ge, X.; Chen, X.; Qian, C.; Zhou, S. RSC Adv. 2016, 6, 58898. doi: 10.1039/C6RA13536F
76. [76]
  Pogula, J.; Laha, S.; Likhar, P. R. Catal. Lett. 2017, 147, 2724. doi: 10.1007/s10562-017-2166-6
77. [77]
  Albadi, J.; Jalali, M.; Samimi, H. A. Catal. Lett. 2018, 148, 3750. doi: 10.1007/s10562-018-2567-1
78. [78]
  Singh, G.; Kumar, M.; Bhalla, V. Green Chem. 2018, 20, 5346. doi: 10.1039/C8GC02527D
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