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

  • 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.
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    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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