Citation: Lianyue Wang, Bo Chen, Lanhui Ren, Henyun Zhang, Ying Lü, Shuang Gao. Vanadium catalyzed direct synthesis of imines from amines or alcohols and amines by an aerobic oxidative reaction under mild conditions[J]. Chinese Journal of Catalysis, ;2015, 36(1): 19-23. doi: 10.1016/S1872-2067(14)60196-0 shu

Vanadium catalyzed direct synthesis of imines from amines or alcohols and amines by an aerobic oxidative reaction under mild conditions

Lianyue Wang ^a ,
Bo Chen ^a,b ,
Lanhui Ren ^a,b ,
Henyun Zhang ^a ,
Ying Lü ^a ,
Shuang Gao ^a,,

1.
a Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China;

Corresponding author: Shuang Gao,
Received Date: 20 June 2014
Available Online: 16 July 2014
Fund Project: 国家重点基础研究发展计划(973计划, 2009CB623505). (973计划, 2009CB623505)

The direct synthesis of imines from amines or alcohols and amines by vanadium catalyzed aerobic oxidation was developed. Without an additive or promoter, various symmetrical and unsymmetrical imines were obtained in good to excellent yields under mild conditions with air as an environmentally benign oxidant. The catalyst is very easy to prepare and use, and this catalytic system is also effective for the synthesis of heteroatom-containing imines.
- Imine,
- Alcohol,
- Amine,
- Aerobic oxidation,
- Vanadium
1. [1]
  [1] Murahashi S I. Angew Chem Int Ed, 1995, 34: 2443
2. [2]
  [2] Gawronski J, Wascinska N, Gajewy J. Chem Rev, 2008, 108: 5227
3. [3]
  [3] Adams J P. J Chem Soc, Perkin Trans 1, 2000: 125
4. [4]
  [4] Layer R W. Chem Rev, 1963, 63: 489
5. [5]
  [5] Gawronski J, Wascinska N, Gajewy J. Chem Rev, 2008, 108: 5227
6. [6]
  [6] Taguchi K, Westheimer F H. J Org Chem, 1971, 36: 1570
7. [7]
  [7] Das B, Ravikanth B, Laxminarayana K, Rao B V. J Mol Catal A, 2006, 253: 92
8. [8]
  [8] Sun H, Su F Z, Ni J, Cao Y, He H Y, Fan K N. Angew Chem Int Ed, 2009, 48: 4390
9. [9]
  [9] Kegnæs S, Mielby J, Mentzel U V, Christensen C H, Riisager A. Green Chem, 2010, 12: 1437
10. [10]
  [10] Gnanaprakasam B, Zhang J, Milstein D. Angew Chem Int Ed, 2010, 49: 1468
11. [11]
  [11] Su F Z, Mathew S C, Mohlmann L, Antonietti M, Wang X C, Blechert S. Angew Chem Int Ed, 2011, 50: 657
12. [12]
  [12] Grirrane A, Corma A, Garcia H. J Catal, 2009, 264: 138
13. [13]
  [13] Zhu B L, Angelici R J. Chem Commun, 2007: 2157
14. [14]
  [14] So M H, Liu Y G, Ho C M, Che C M. Chem Asian J, 2009, 4: 1551
15. [15]
  [15] Gunanathan C, Ben-David Y, Milstein D. Science, 2007, 317: 790
16. [16]
  [16] Watson A J A, Williams J M J. Science, 2010, 329: 635
17. [17]
  [17] Watson A J A, Maxwell A C, Williams J M J. Org Lett, 2009, 11: 2667
18. [18]
  [18] Bala M, Verma P K, Kumar N, Sharma U, Singh B. Can J Chem, 2013, 91: 732
19. [19]
  [19] Perez J M, Cano R, Yus M, Ramon D J. Eur J Org Chem, 2012, 2012: 4548
20. [20]
  [20] Cano R, Ramon D J, Yus M. J Org Chem, 2011, 76: 5547
21. [21]
  [21] Tang L, Sun H Y, Li Y F, Zha Z G, Wang Z Y. Green Chem, 2012, 14: 3423
22. [22]
  [22] Reddy M M, Kumar M A, Swamy P, Naresh M, Srujana K, Satyanarayana L, Venugopal A, Narender N. Green Chem, 2013, 15: 3474
23. [23]
  [23] Blackburn L, Taylor R J K. Org Lett, 2001, 3: 1637
24. [24]
  [24] Yusubov M S, Chi K W, Park J Y, Karimov R, Zhdankin V V. Tetrahedron Lett, 2006, 47: 6305
25. [25]
  [25] Kwon M S, Kim S, Park S, Bosco W, Chidrala R K, Park J. J Org Chem, 2009, 74: 2877
26. [26]
  [26] Cui W J, Bao Z, Jia M L, Ao W L, Zhu H Y. RSC Adv, 2014, 4: 2601
27. [27]
  [27] Furukawa S, Suga A, Komatsu T. Chem Commun, 2014, 50: 3277
28. [28]
  [28] He W, Wang L D, Sun C L, Wu K K, He S B, Chen J P, Wu P, Yu Z K. Chem Eur J, 2011, 17: 13308
29. [29]
  [29] Soule J F, Miyamura H, Kobayashi S. Chem Commun, 2013, 49: 355
30. [30]
  [30] Zhang L L, Wang W T, Wang A Q, Cui Y T, Yang X F, Huang Y Q, Liu X Y, Liu W G, Son J Y, Oji H, Zhang T. Green Chem, 2013, 15: 2680
31. [31]
  [31] Neeli C K P, Ganji S, Ganjala V S P, Kamaraju S R R, Burri D R. RSC Adv, 2014, 4: 14128
32. [32]
  [32] Mielby J, Poreddy R, Engelbrekt C, Kengnæs S. Chin J Catal (催化学报), 2014, 35: 670
33. [33]
  [33] Kim J W, He J L, Yamaguchi K, Mizuno N. Chem Lett, 2009, 38: 920
34. [34]
  [34] Chem B, Li J, Dai W, Wang L Y, Gao S. Green Chem, 2014, 16: 3328
35. [35]
  [35] Zhang E L, Tian H W, Xu S D, Yu X C, Xu Q. Org Lett, 2013, 15: 2704
36. [36]
  [36] Kang Q, Zhang Y G. Green Chem, 2012, 14: 1016
37. [37]
  [37] Huang B, Tian H W, Lin S S, Xie M H, Yu X C, Xu Q. Tetrahedron Lett, 2013, 54: 2861
38. [38]
  [38] Tian H W, Yu X C, Li Q, Wang J X, Xu Q. Adv Synth Catal, 2012, 354: 2671
39. [39]
  [39] Wang J Q, Lu S L, Cao X Q, Gu H W. Chem Commun, 2014, 50: 5637
40. [40]
  [40] Jiang L, Jin L L, Tian H W, Yuan X Q, Yu X C, Xu Q. Chem Commun, 2011, 47: 10833
41. [41]
  [41] Qiu X, Len C, Luque R, Li Y W. ChemSusChem, 2014, 7: 1684
42. [42]
  [42] Punniyamurthy T, Velusamy S, Iqbal J. Chem Rev, 2005, 105: 2329
43. [43]
  [43] Kodama S, Yoshida J, Nomoto A, Ueta Y, Yano S, Ueshima M, Ogawa A. Tetrahedron Lett, 2010, 51: 2450
44. [44]
  [44] Hanson S K, Wu R L, Silks L A P. Org Lett, 2011, 13: 1908
45. [45]
  [45] Hanson S K, Wu R L, Silks L A P. Angew Chem Int Ed, 2012, 51: 3410
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