Citation: Wang Hui, Huang Longjiang. Progress in Imine Formation from Direct Coupling of Alcohols and Amines Catalyzed by Metal Catalysts[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 883-902. doi: 10.6023/cjoc201808039 shu

Progress in Imine Formation from Direct Coupling of Alcohols and Amines Catalyzed by Metal Catalysts

Wang Hui ,
Huang Longjiang ^,

College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042

Corresponding author: Huang Longjiang, huanglj@qust.edu.cn
Received Date: 30 August 2018
Revised Date: 14 November 2018
Available Online: 5 April 2018
Fund Project: Project supported by the Higher Educational Science and Technology Program of Shandong Province (No. J16LC13)the Higher Educational Science and Technology Program of Shandong Province J16LC13

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Imines are very important class of compounds and have been widely utilized in fine chemicals, pharmaceuticals and chemical industry. The C=N double bond in imine is an important nitrogen source in different types of reactions due to its high reactive activity. Due to its high atom economy, catalytic direct coupling of alcohols and amines to imines based on metal catalysts has attracted much attention and maken great progress in recent years. In this paper, the advances in direct coupling of alcohols and amines to imines catalyzed by metal catalysts are reviewed.
- imine,
- alocohols,
- amines,
- metal catalysis
1. [1]
  Marques, C. S.; Burke, A. J. ChemInform 2011, 3, 635.
2. [2]
  Bayrak, H.; Demirbas, A.; Karaoglu, S. A.; Demirbas, N. Eur. J. Med. Chem. 2009, 44, 1057. doi: 10.1016/j.ejmech.2008.06.019
3. [3]
  Gawronski, J.; Wascinska, N.; Gajewy, J. Chem. Rev. 2008, 108, 5227. doi: 10.1021/cr800421c
4. [4]
  Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626. doi: 10.1021/cr100204f
5. [5]
  And, S. K.; Ishitani, H. Chem. Rev. 1999, 99, 1069. doi: 10.1021/cr980414z
6. [6]
  Nielsen, M.; Worgull, D.; Zweifel, T.; Gschwend, B.; Bertelsen, S.; Jørgensen, K. A. Chem. Commun. 2011, 47, 632. doi: 10.1039/C0CC02417A
7. [7]
  Marques, C. S.; Burke, A. J. ChemCatChem 2011, 3, 635. doi: 10.1002/cctc.201000369
8. [8]
  Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 4916. doi: 10.1021/ja960364k
9. [9]
  Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. ChemInform 2010, 33, 9692.
10. [10]
  Nieto, S.; Dragna, J. M.; Anslyn, E. V. Chem.-Eur. J. 2010, 16, 227. doi: 10.1002/chem.v16:1
11. [11]
  Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. ChemCatChem 2010, 2, 1438. doi: 10.1002/cctc.201000175
12. [12]
  Nakajima, R.; Ogino, T.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2010, 132, 1236. doi: 10.1021/ja9103233
13. [13]
  Hadjipavlou-Litina, D. J.; Geronikaki, A. A. Drug Des. Discovery 1998, 15, 199.
14. [14]
  Akhmetova, V. R.; Khabibullina, G. R.; Rakhimova, E. B. Mol. Diversity 2010, 14, 463. doi: 10.1007/s11030-010-9248-3
15. [15]
  Nielsen, M.; Worgull, D.; Zweifel, T.; Gschwend, B.; Bertelsen, Jørgensen, K. A. Chem. Commun. 2011, 47, 632. doi: 10.1039/C0CC02417A
16. [16]
  Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626. doi: 10.1021/cr100204f
17. [17]
  Xie, J. H.; Zhu, S. F.; Zhou, Q. L. Chem. Rev. 2011, 111, 1713. doi: 10.1021/cr100218m
18. [18]
  Marques, C. S.; Burke, A. J. ChemCatChem. 2011, 3, 635. doi: 10.1002/cctc.201000369
19. [19]
  Nieto, S.; Dragna, J. M.; Anslyn, E. V. Chem.-Eur. J. 2010, 16, 227. doi: 10.1002/chem.v16:1
20. [20]
  Dhakshinamoorthy, A.; Alvaro, M. ChemCatChem 2010, 2, 1438. doi: 10.1002/cctc.201000175
21. [21]
  Aschwanden, L.; Mallat, T.; Maciejewski, M.; Krumeich, F.; Baiker, A. ChemCatChem 2010, 2, 666. doi: 10.1002/cctc.201000092
22. [22]
  Min, S. K.; Kim, S.; Park, S.; Park, S.; Bosco, W.; Chidrala, R. K.; Park, J. J. Org. Chem. 2009, 74, 2877. doi: 10.1021/jo8026609
23. [23]
  Jiang, L.; Jin, L. L.; Tian, H. W.; Yuan, X. Q.; Yu, X. C.; Xu, Q. Chem. Commun. 2011, 47, 10833. doi: 10.1039/c1cc14242a
24. [24]
  Chen, G. J.; Ma, H. C.; Xin, W. L.; Li, X. B.; Jin, F. Z.; Wang, J. S.; Liu, M. Y.; Dong, Y. B. Inorg. Chem. 2017, 56, 654. doi: 10.1021/acs.inorgchem.6b02592
25. [25]
  Tian, H. W.; Yu, X. C.; Li, Q.; Wang, J. X.; Xu, Q. Adv. Synth. Catal. 2012, 354, 2671. doi: 10.1002/adsc.v354.14/15
26. [26]
  Kang, Q.; Zhang, Y. G. Green Chem. 2012, 43, 1016.
27. [27]
  Bai, L.; Dang, Z. RSC Adv. 2015, 5, 10341. doi: 10.1039/C4RA14890H
28. [28]
  Darapanani, C. M.; Arghya, S.; Galia, M. J. Catal. 2017, 355, 139. doi: 10.1016/j.jcat.2017.09.018
29. [29]
  Wei, Y. G.; Yu, H.; Zhai, Y. Y.; Dai, G. Y.; Ru, S.; Han, S. Chem.-Eur. J. 2017, 23, 13883. doi: 10.1002/chem.201703185
30. [30]
  And, L. B.; Taylor R, J. K. Org. Lett. 2001, 4, 1637.
31. [31]
  Sithambaram, S.; Kumar, R.; Son, Y. C.; Steven, L. J. Catal. 2008, 253, 269. doi: 10.1016/j.jcat.2007.11.006
32. [32]
  Mondal, J.; Borah, P.; Sreejith, S.; Nguyen, K. T.; Han, X. G.; Ma, X.; Zhao, Y. L. ChemCatChem 2014, 6, 3518. doi: 10.1002/cctc.201402512
33. [33]
  Chen, B.; Li, J.; Dai, W.; Wang, L. Y.; Gao, S. Green Chem. 2014, 16, 3328. doi: 10.1039/c4gc00336e
34. [34]
  Zhang, E, L.; Tian, H. W.; Xu, S. D.; Yu, X. C.; Xu, Q. Org. Lett. 2013, 15, 2704. doi: 10.1021/ol4010118
35. [35]
  Geng, L. L.; Song, J. L.; Zheng, B.; Wu, S. J.; Zhang, W. X.; Jia, M. J.; Liu, G. Chin. J. Catal. 2016, 37, 1451. doi: 10.1016/S1872-2067(16)62506-8
36. [36]
  Sindhuja, E.; Ramesh, R. Tetrahedron Lett. 2014, 55, 5504. doi: 10.1016/j.tetlet.2014.08.035
37. [37]
  Sun, H.; Su, F. Z.; Ni, J.; Cao, Y.; He, H. Y.; Fan, K. N. Angew. Chem., Int. Ed. 2009, 48, 4390. doi: 10.1002/(ISSN)1521-3773
38. [38]
  Kegnæs, S.; Mielby, J.; Mentzel, U. V.; Christensen, C. H.; Riisager, A. Green Chem. 2010, 12, 1437. doi: 10.1039/c0gc00126k
39. [39]
  Liu, P.; Li, C.; Hensen, E. J. Chem.-Eur. J. 2012, 18, 12122. doi: 10.1002/chem.201202077
40. [40]
  Soulé, J. F.; Miyamura, H.; Kobayashi, S. Chem. Commun. 2013, 49, 355. doi: 10.1039/C2CC36213A
41. [41]
  Huang, R.; Yang, Y.; Wang, D. S.; Zhang, L.; Wang, D. W. Org. Chem. Front. 2017, 5, 203.
42. [42]
  Han, L.; Xing, P.; Jiang, B. Org. Lett. 2014, 16, 3428. doi: 10.1021/ol501353q
43. [43]
  Mielby, J.; Poreddy, R.; Engelbrekt, C.; Kegnæs, S. Chin. J. Catal. 2014, 35, 670. doi: 10.1016/S1872-2067(14)60033-4
44. [44]
  Zhang, G. Q.; Hanson, S. K. Org. Lett. 2013, 15, 650. doi: 10.1021/ol303479f
45. [45]
  Sun, Y. W.; Lu, X. H.; Wei, X. L.; Zhou, D.; Xia, Q. H. Catal. Commun. 2014, 43, 213. doi: 10.1016/j.catcom.2013.10.008
46. [46]
  Midya, S. P.; Pitchaimani, J.; Landge, V. G.; Madhu, V.; Ekam-baram, B. Catal. Sci. Technol. 2018, 8, 3469. doi: 10.1039/C8CY00859K
47. [47]
  Xu, C.; Lai, Goh, L. Y.; Pullarkat, S. A. Organometallics. 2011, 30, 6499. doi: 10.1021/om200883e
48. [48]
  Chang, Y. H.; Tanigawa, I.; Takeuchi, K.; Taguchi, H.; Ozawa, F. Eur. J. Inorg. Chem. 2016, 5, 754.
49. [49]
  Gnanaprakasam, B.; Zhang, J.; Milstein, D. Angew. Chem., Int. Ed. 2010, 49, 1468. doi: 10.1002/anie.200907018
50. [50]
  Cano, R.; Ramón, D. J.; Yus, M. J. Org. Chem. 2011, 76, 5547. doi: 10.1021/jo200559h
51. [51]
  Maggi, A.; Madsen, R. Organometallics 2012, 31, 451. doi: 10.1021/om201095m
52. [52]
  Jared, W. R.; Sara, A. M.; Simon, D. P.; Jennifer, M. S. Org. Biomol. Chem. 2012, 10, 1746. doi: 10.1039/c2ob06921k
53. [53]
  Musa, S.; Fronton, S.; Vaccaro, L.; Gelman, D. Organometallics 2013, 32, 3069. doi: 10.1021/om400285r
54. [54]
  Saha, B.; Daw, P.; Sengupta, G.; Rahaman, S. M.; Bera, J. K. Chem.-Eur. J. 2014, 20, 6542. doi: 10.1002/chem.201304403
55. [55]
  Oldenhuis, N. J.; Dong, V. M.; Guan. Z. B. Tetrahedron 2014, 70, 4213. doi: 10.1016/j.tet.2014.03.085
56. [56]
  Higuchi, T.; Tagawa, R.; Iimuro, A.; Akiyama, S.; Nagae, H.; Mashima, K. Chem.-Eur. J. 2017, 23, 12795. doi: 10.1002/chem.v23.52
57. [57]
  Yu, X. J.; Li, Y. Q.; Fu, H. Y.; Zheng, X. L.; Chen, H.; Li, R. X. Appl. Organomet. Chem. 2018, 32, 4277. doi: 10.1002/aoc.v32.4
58. [58]
  Shiraishi, Y.; Ikeda, M.; Tsukamoto, D.; Tanaka, S.; Hirai, T. Chem. Commun. 2011, 47, 4811. doi: 10.1039/c0cc05615d
59. [59]
  Pérez, J. M.; Cano, R.; Yus, M.; Ramón, D. J. Eur. J. Org. Chem. 2012, 24, 4548.
60. [60]
  Tang, L.; Sun, H. Y.; Li, Y. F.; Zha, Z. G.; Wang, Z. Y. Green Chem. 2012, 14, 3423. doi: 10.1039/c2gc36312g
61. [61]
  Wang, H.; Zhang, J.; Cui, Y. M.; Yang, K. F.; Zheng, Z. J.; Xu, L. W. RSC. Adv. 2014, 4, 34681. doi: 10.1039/C4RA06685E
62. [62]
  Bain, J.; Cho, P.; Voutchkova-Kostal, A. Green Chem. 2015, 17, 2271. doi: 10.1039/C5GC00312A
63. [63]
  Jaiswal, G.; Landge, V. G.; Jagadeesan, D.; Balaraman, E. Green Chem. 2016, 47, 3232.
64. [64]
  Mukherjee, A.; Nerush, A.; Leitus, G.; Shimon L, J. W.; David, Y. B.; Jalapa N, A. E.; Milstein, D. J. Am. Chem. Soc. 2016, 138, 4298. doi: 10.1021/jacs.5b13519
65. [65]
  Mastalir, M.; Glatz, M.; Gorgas, N.; Stçger, B.; Pittenauer, E.; Allmaier, G.; Veiros, L. F.; Kirchner, K. Chem.-Eur. J. 2016, 22, 12316. doi: 10.1002/chem.v22.35
66. [66]
  Fertig, R.; Irrgang, T.; Freitag, F.; Zander, J.; Kempe, R. ACS Catal. 2018, 9, 8525.
67. [67]
  Esteruelas, M. A.; Honczek, N.; Valencia, M.; Oñate, E.; Oliván, M. Organometallics 2011, 30, 2468. doi: 10.1021/om200290u
68. [68]
  Madsen, R.; Azizi, K. ChemCatChem 2018, 53, 1.
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