Citation: Liu Di, Zhang Chenghui, Han Nan, Du Mengmeng, Zhang Xiaolu, Zhao Pengshan, Yang Ping. Progress in Oxidative Coupling of Amines to Imines[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1350-1363. doi: 10.6023/cjoc201801017 shu

Progress in Oxidative Coupling of Amines to Imines

College of Chemical and Environmental Engineering, Shandong University of Science and Technology, Qingdao 266590

Corresponding author: Liu Di, ld002037132@163.com
Received Date: 9 January 2018
Revised Date: 9 February 2018
Available Online: 11 June 2018
Fund Project: Project supported by the Open Foundation of the State Key Laboratory of Bioactive Seaweed Substances (No. SKL-BASS1723)the Open Foundation of the State Key Laboratory of Bioactive Seaweed Substances SKL-BASS1723

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Imines are a class of active intermediates and have good antibacterial activity, therefore, they have received the extensive concern of scientists. Since the preparation method of imines by oxidative coupling of amines has the advantages of high atom economy and environmental friendliness, it has become a research hotspot. The recent progress in oxidative coupling of amines to imines is summarized from two aspects:catalyst and catalytic mechanism in this article. We introduced all kinds of catalytic systems in detail such as noble metal, non-noble metal, photocatalysis, biomimetic catalysis, poly aniline, graphite oxide, and azobisisobutyronitrile (AIBN). The catalytic performance, advantages and drawbacks and applicability of which are highlighted. And the catalytic mechanisms of the main catalytic systems are also discussed. It should be pointed out that these catalytic systems for oxidative coupling of amines to imines showed varying degrees of success as well as limitations like high cost of catalyst, harsh reaction condition, use of oxidant, alkaline additives and/or toxic organic solvents. Finally, based on the existential problems for oxidative coupling of amines to imines, the research directions in this field are predicted.
- amines,
- oxidation coupling,
- imines,
- transition-metal catalysis,
- photocatalysis,
- biomimetic catalysis
1. [1]
  Kobayashi, S.; Mori, Y.; Fossey, J. -S.; Salter, M. -M. Chem. Rev. 2011,111, 2626. doi: 10.1021/cr100204f
2. [2]
  Adams, J. -P. J. Chem. Soc. ,Perkin Trans. 1 2000, 125.
3. [3]
  Ashok, M.; Holla, B. -S.; Poojary, B. Eur. J. Med. Chem. 2007,46, 1095.
4. [4]
  Young, J. -N.; Chang, T. -C.; Tsai, S. -C.; Yang, L.; Yu, S. -C. J. Catal. 2010,272, 253. doi: 10.1016/j.jcat.2010.04.005
5. [5]
  Santos, L. -L.; Serna, P.; Corma, A. Chem. -Eur. J. 2009,15, 8196. doi: 10.1002/chem.v15:33
6. [6]
  Zanardi, A.; Mata, J. -A.; Peris, E. Chem. -Eur. J. 2010,16, 10502. doi: 10.1002/chem.201000801
7. [7]
  Maggi, A.; Madsen, R. Organometallics 2012,31, 451. doi: 10.1021/om201095m
8. [8]
  Kwon, M. -S.; Kim, S.; Park, S.; BoscoO, W.; Chidrala, R. -K.; Park, J. J. Org. Chem. 2009,74, 2877. doi: 10.1021/jo8026609
9. [9]
  Jiang, G.; Chen, J.; Huang, J. -S.; Che, C. -M. Org. Lett. 2009,11, 4568. doi: 10.1021/ol9018166
10. [10]
  Bailey, A. -J.; James, B. -R. Chem. Commun. 1996,0, 2343.
11. [11]
  Prades, A.; Peris, E.; Albrecht, M. Organometallics 2011,30, 1162. doi: 10.1021/om101145y
12. [12]
  Doctorovich, F.; Granara, M.; Salvo, F. -D. TransitionMet. Chem. 2001,26, 505. doi: 10.1023/A:1011033312510
13. [13]
  He, L. -P.; Chen, T.; Gong, D.; Lai, Z.; Huang, K. -W. Organometallics 2012,31, 5208. doi: 10.1021/om300422v
14. [14]
  Zhang, Y. -C.; Lu, F.; Huang, R.; Zhang, H. -Y.; Zhao, J. -Q. Catal. Commun. 2016,81, 10. doi: 10.1016/j.catcom.2016.03.019
15. [15]
  Zhu, B.; Angelici, R. -J. Chem. Commun. 2007,38, 2157.
16. [16]
  Zhu, B.; Lazar, M.; Trewyn, B. -G.; Angelici, R. -J. J. Catal. 2008,260, 1. doi: 10.1016/j.jcat.2008.08.012
17. [17]
  Grirrane, A.; Corma, A.; Garcia, H. J. Catal. 2009,264, 138. doi: 10.1016/j.jcat.2009.03.015
18. [18]
  Pérez, Y.; Aprile, C.; Corma, A.; Garcia, H. Catal Lett. 2010,134, 204. doi: 10.1007/s10562-009-0243-1
19. [19]
  Ishida, T.; Kawakita, N.; Akita, T.; Haruta, M. Gold Bull. 2009,42, 267. doi: 10.1007/BF03214948
20. [20]
  Srimani, D.; Feller, M.; Ben-David, Y.; Milstein, D. Chem. Commun. 2012,48, 11853. doi: 10.1039/c2cc36639h
21. [21]
  Lu, S. -L.; Wang, J. Q.; Cao, X. Q.; Li, X. M.; Gu, H. W. Chem. Commun. 2014,50, 3512. doi: 10.1039/C3CC48596J
22. [22]
  Patil, R. -D.; Adimurthy, S. Adv. Synth. Catal. 2011,353, 1695. doi: 10.1002/adsc.201100100
23. [23]
  Patil, R. -D, Adimurthy, S. RSC Adv. 2012,2, 5119. doi: 10.1039/c2ra20339a
24. [24]
  Patil, R. -D, Adimurthy, S. Asian J. Org. Chem. 2013,2, 726. doi: 10.1002/ajoc.v2.9
25. [25]
  Hu, Z. -Z.; Kerton, F. -M. Org. Biomol. Chem. 2012,10, 1618. doi: 10.1039/c2ob06670j
26. [26]
  Huang, B.; Tian, H.; Lin, S.; Xie, M.; Yu, X.; Xu, Q. Tetrahedron Lett. 2013,54, 2861. doi: 10.1016/j.tetlet.2013.03.098
27. [27]
  Largeron, M.; Fleury, M. -B. Chem. -Eur. J. 2015,21, 1.
28. [28]
  Wang, J.; Lu, S.; Cao, X.; Gu, H. Chem. Commun. 2014,50, 5637. doi: 10.1039/c4cc01389a
29. [29]
  Al-Hmoud, L.; Jones, C. -W. J. Catal. 2013,301, 116. doi: 10.1016/j.jcat.2013.01.027
30. [30]
  Marui, K.; Nomoto, A.; Ueshima, M.; Ogawa, A. Tetrahedron Lett. 2015,56, 1200. doi: 10.1016/j.tetlet.2015.01.090
31. [31]
  Chu, G. -B.; Li, C. -B. Org. Biomol. Chem. 2010,8, 4716. doi: 10.1039/c0ob00043d
32. [32]
  Wang, L. -Y.; Chen, B.; Ren, L. -H.; Zhang, H. -Y.; Lü, Y.; Gao, S. Chin. J. Catal. 2015,36, 19. doi: 10.1016/S1872-2067(14)60196-0
33. [33]
  Kodama, S.; Yoshida, J.; Nomoto, A.; Ueta, Y.; Yano, S.; Ueshima, M.; Ogawa, A. Tetrahedron Lett. 2010,41, 2450.
34. [34]
  Neumann, R.; Levin, M. -J. J. Org. Chem. 1991,56, 5707. doi: 10.1021/jo00019a047
35. [35]
  Nakayama, K.; Hamamoto, M.; Nishiyama, Y.; Ishii, Y. Chem. Lett. 1993,22, 1699. doi: 10.1246/cl.1993.1699
36. [36]
  Reddy, J. -S.; Sayari, A. Catal. Lett. 1994,28, 263. doi: 10.1007/BF00806055
37. [37]
  Maruyama, K.; Kusukawa, T.; Highchi, Y.; Nishinaga, A. Chem. Lett. 1991,7, 1093.
38. [38]
  Zhao, S.; Liu, C.; Guo, Y.; Xiao, J. -C.; Chen, Q. -Y. J. Org. Chem. 2014,79, 8926. doi: 10.1021/jo5017212
39. [39]
  Zhang, C. -H.; Zhao, P. -S.; Zhang, Z. -L.; Zhang, J. -W.; Yang, P.; Gao, P.; Gao, J.; Liu, D. RSC Adv. 2017,7, 47366. doi: 10.1039/C7RA09516C
40. [40]
  Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. ChemCatChem 2010,2, 1438. doi: 10.1002/cctc.201000175
41. [41]
  Zhang, E.; Tian, H. -W.; Xu, S. -D.; Yu, X. -C.; Xu, Q. Org. Lett. 2013,15, 2704. doi: 10.1021/ol4010118
42. [42]
  Gopalaiah, K.; Saini, A. Catal. Lett. 2016,146, 1648. doi: 10.1007/s10562-016-1789-3
43. [43]
  Kim, S. -S.; Thakur, S. -S.; Song, J. -Y.; Lee, K. -H. Bull. Korean Chem. Soc. 2005,26, 499. doi: 10.5012/bkcs.2005.26.3.499
44. [44]
  Choudary, B. -M.; Narender, N.; Bhuma, V. Synth. Commun. 1996,26, 631. doi: 10.1080/00397919608086735
45. [45]
  Ohtani, B.; Osaki, H.; Nishimoto, S. -I.; Kagia, T. Chem. Lett. 1985,21, 1075.
46. [46]
  Lang, X.; Ji, H.; Chen, C.; Ma, W.; Zhao, J. Angew. Chem. ,Int. End. 2011,50, 3934. doi: 10.1002/anie.201007056
47. [47]
  Lang, X.; Ma, W.; Zhao, Y.; Chen, C.; Ji, H.; Zhao, J. Chem. -Eur. J. 2012,18, 2624. doi: 10.1002/chem.201102779
48. [48]
  Li, N.; Lang, X. -J.; Ma, W. -H.; Ji, H. -W.; Chen, C. -C.; Zhao, J. -C. Chem. Commun. 2013,49, 5034. doi: 10.1039/c3cc41407h
49. [49]
  Bu, J.; Fang, J.; Leow, W. -R.; Zheng, K. -H.; Chen, X. -D. RSC Adv. 2015,5, 103895. doi: 10.1039/C5RA23428J
50. [50]
  Dai, J.; Yang, J.; Wang, X. -H.; Zhang, L.; Li, Y. Appl. Surf. Sci. 2015,349, 343. doi: 10.1016/j.apsusc.2015.04.232
51. [51]
  Zavahir, S.; Zhu, H. Molecules 2015,20, 1941. doi: 10.3390/molecules20021941
52. [52]
  Furukawa, S.; Ohno, Y.; Shishido, T.; Teramura, K.; Tanaka, T. ACS Catal. 2011, 1, 1150. doi: 10.1021/cs200318n
53. [53]
  Su, F.; Mathew, S. -C.; Möhlmann, L.; Antonietti, M.; Wang, X.; Blechert, S. Angew. Chem. ,Int. Ed. 2011,50, 657. doi: 10.1002/anie.v50.3
54. [54]
  Park, J. -H.; Ko, K. -C.; Kim, E.; Park, N.; Ko, J. -H.; Ryu, D. -H.; Ahn, T. -K.; Lee, J. -Y.; Son, S. -U. Org. Lett. 2012,14, 5502. doi: 10.1021/ol302584y
55. [55]
  Jin, J.; Shin, H. -W.; Park, J. -H.; Park, J. -H.; Kim, E.; Ahn, T. -K.; Ryu, D. -H.; Son, S. -U. Organometallics 2013,32, 3954. doi: 10.1021/om4004412
56. [56]
  Berlicka, A.; König, B. Photochem. Photobiol. Sci. 2010,9, 1359. doi: 10.1039/c0pp00192a
57. [57]
  Naya, S. -I.; Kimura, K.; Tada, H. ACS Catal. 2013,3, 10. doi: 10.1021/cs300682d
58. [58]
  Ye, L.; Li, Z. -H. ChemCatChem 2014,6, 2540. doi: 10.1002/cctc.201402360
59. [59]
  Mure, M.; Klinman, J. -P. J. Am. Chem. Soc. 1995,117, 8698. doi: 10.1021/ja00139a002
60. [60]
  Mure, M.; Klinman, J. -P. J. Am. Chem. Soc. 1995,117, 8707. doi: 10.1021/ja00139a003
61. [61]
  Lee, Y.; Sayre, L. -M. J. Am. Chem. Soc. 1995,117, 11823. doi: 10.1021/ja00153a001
62. [62]
  Ling, K. -Q.; Kim, J.; Sayre, L. -M. J. Am. Chem. Soc. 2001,123, 9606. doi: 10.1021/ja011141j
63. [63]
  Wendlandt, A. -E.; Stahl, S. -S. Org. Lett. 2012,14, 2850. doi: 10.1021/ol301095j
64. [64]
  Yuan, H.; Yoo, W. -J.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2012,134, 13970. doi: 10.1021/ja306934b
65. [65]
  Yuan, Q. -L.; Zhou, X. -T.; Ji, H. -B. Catal. Commun. 2010,12, 202. doi: 10.1016/j.catcom.2010.09.009
66. [66]
  Tollari, S.; Fumagalli, A.; Porta, F. Inorg. Chim. Acta 1997,247, 71.
67. [67]
  Kim, S. -S.; Thakur, S. -S.; Bull, K. Chem. Soc. 2005,26, 1600.
68. [68]
  Zhou, X. -T.; Ren, Q. -G.; Ji, H. -B. Tetrahedron Lett. 2012,53, 3369. doi: 10.1016/j.tetlet.2012.04.096
69. [69]
  Higuchi, M.; Ikeda, I.; Hirao, T. J. Org. Chem. 1997,62, 1072. doi: 10.1021/jo9617575
70. [70]
  Huang, H.; Huang, J.; Liu, Y. -M.; He, H. -Y.; Cao, Y.; Fan, K. -N. Green Chem. 2012,14, 930. doi: 10.1039/c2gc16681j
71. [71]
  Landge, S. -M.; Atanassova, V.; Thimmaiah, M.; Török, B. Tetrahedron Lett. 2007,48, 5161. doi: 10.1016/j.tetlet.2007.05.051
72. [72]
  Liu, L.; Wang, Z.; Fu, X.; Yan, C. -H. Org. Lett. 2012,14, 5692. doi: 10.1021/ol302708r
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