Citation: Wang Kehu, Wang Yalin, Yin Xuejiao, Peng Xiansha, Huang Danfeng, Su Yingpeng, Hu Yulai. Tin-Promoted One-Pot Synthesis of Aryl/Trifluoromethyl Group Substituted Homoallylic N-Acylhydrazines[J]. Chinese Journal of Organic Chemistry, ;2017, 37(7): 1764-1773. doi: 10.6023/cjoc201612042 shu

Tin-Promoted One-Pot Synthesis of Aryl/Trifluoromethyl Group Substituted Homoallylic N-Acylhydrazines

  • Corresponding author: Wang Kehu, wangkh@nwnu.edu.cn Hu Yulai, huyl@nwnu.edu.cn
  • Received Date: 13 December 2016
    Revised Date: 1 March 2017
    Available Online: 14 July 2017

    Fund Project: National Natural Science Foundation of China 21262031National Natural Science Foundation of China 21462037Project supported by the National Natural Science Foundation of China (Nos. 21262031, 21462037)

  • A series of trifluoromethylated homoallylic N-acylhydrazines were obtained from one-pot reaction of aryl trifluoroketones, acylhydrazines and allyl bromide promoted by tin powder in the presence of boron trifluoride diethyl etherate (BF3·OEt2). The features of this process include good yields, wide substrate scope, mild conditions and easy operation. Trifluoromethylated homoallylic N-acylhydrazines are useful trifluoromethyl building blocks. They can be easily transformed into trifluoromethylated nitrogen-containing compounds.
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    1. [1]

    2. [2]

      (a) Cametti, M.; Crousse, B.; Metrangolo, P. Chem. Soc. Rev. 2012, 41, 31.
      (b) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.

    3. [3]

      (a) Li, Y. Acc. Chem. Res. 2012, 45, 723.
      (b) Jeschke, P. ChemBioChem 2004, 5, 570.

    4. [4]

    5. [5]

      (a) Shi, M.; Liu, X.-G.; Guo, Y.-W.; Zhang, W. Tetrahedron 2007, 63, 12731.
      (b) Corey, E. J.; Cheng, X.-M.; Cimprich, K. A.; Sarshar, S. Tetrahedron Lett. 1991, 32, 6835.

    6. [6]

      (a) Zheng, Y.; Ma, H.; Ma, J. A. Chin. J. Chem. 2016, 34, 511.
      (b) Zhang, S.; Li, L.; Hu, Y.; Li, Y.; Yang, Y.; Zha, Z.; Wang, Z. Org. Lett. 2015, 17, 5036.
      (c) Zhang, G.-W.; Meng, W.; Ma, H.; Nie, J.; Zhang, W.-Q.; Ma, J.-A. Angew. Chem., Int. Ed. 2011, 123, 3600.
      (d) Wang, X.-N.; Shao, P.-L.; Lv, H.; Ye, S. Org. Lett. 2009, 11, 4029.

    7. [7]

      (a) Curran, S. P.; Connon S. J. Org. Lett. 2012, 14, 1074.
      (b) Cronin, L.; Manoni, F.; O'Connor, C. J.; Connon, S. J. Angew. Chem., Int. Ed. 2010, 49, 3045.

    8. [8]

      (a) Tao, R.; Yin, X.-J.; Wang, K.-H.; Niu, Y.-Z.; Wang, Y.-L.; Huang, D.-F.; Su, Y.-P.; Wang, J.-X.; Hu, Y.-L.; Fu, Y.; Du. Z.-Y. Chin. Chem. Lett. 2015, 26, 1046.
      (b) Zhang, D.; Tanaka, F. Adv. Synth. Catal. 2015, 357, 3458.
      (c) Lin, J.; Kang, T.; Liu, Q.; He, L. Tetrahedron:Asymmetry 2014, 25, 949.
      (d) Li, X.-J.; Xiong, H.-Y.; Hua, M.-Q.; Nie, J.; Zheng, Y.; Ma, J.-A. Tetrahedron Lett. 2012, 53, 2117.
      (e) Sasaki, S.; Kikuchi, K.; Yamauchi, T.; Higashiyama, K. Synlett 2011, 1431.

    9. [9]

      Corbett, M. T.; Xu, Q.; Johnson, J. S. Org. Lett. 2014, 16, 2362.  doi: 10.1021/ol500679w

    10. [10]

    11. [11]

      (a) Ding, H.; Frestad, G. K. Org. Lett. 2004, 6, 637.
      (b) Friestad, G. K.; Ding, H. Angew. Chem., Int. Ed. 2001, 40, 4491.
      (c) Dey, S.; Gadakh, S. K.; Ahuja, B. B.; Kamble, S. P.; Sudalai A. Tetrahedron Lett. 2016, 57, 684.

    12. [12]

      (a) Ternon, M.; Quturquin, F.; Paulmier, C. Tetrahedron 2001, 57, 10259.
      (b) Tiecco, M.; Testaferri, L.; Marini, F. Tetrahedron 1996, 52, 11841.

    13. [13]

      (a) Kobayashi, S.; Hamada, H.; Manabe, K. Synlett 2001, 1140.
      (b) Manabe, K.; Oyamada, H.; Sugita, K.; Kobayashi, S. J. Org. Chem. 1999, 64, 8054.

    14. [14]

      Kumar, H. M. S.; Anjaneyulu, S.; Reddy, E. J.; Yadav, J. S. Tetrahedron Lett. 2000, 41, 9311.  doi: 10.1016/S0040-4039(00)01676-2

    15. [15]

      (a) Berger, R.; Rabbat, P. M. A.; Leighton, J. L. J. Am. Chem. Soc. 2003, 125, 9596.
      (b) Hamada, T.; Manabe, K.; Kobayashi, S. Angew. Chem., Int. Ed. 2003, 42, 3927.
      (c) Berger, R.; Duff, K.; Leighton, J. L. J. Am. Chem. Soc. 2004, 126, 5686.
      (d) Friestad, G. K.; Korapala, C. S.; Ding H. J. Org. Chem. 2006, 71, 281.

    16. [16]

    17. [17]

      (a) Cook, G. R.; Maity, B. C.; Kargbo, R. Org. Lett. 2004, 6, 1741.
      (b) Cook, G. R.; Kargbo, R.; Maity, B. Org. Lett. 2005, 7, 2767.
      (c) Tan, K. L.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2007, 46, 1315.

    18. [18]

      Hirabayashi, R.; Ogawa, C.; Sugiura, M.; Kobayashi S. J. Am. Chem. Soc. 2001, 123, 9493.  doi: 10.1021/ja011125m

    19. [19]

      Niu, T.; Zhang, W.; Huang, D.; Xu, C.; Wang, H.; Hu, Y. Org. Lett. 2009, 11, 4474.  doi: 10.1021/ol901886u

    20. [20]

      (a) Wiedemann, J.; Heiner, T.; Mloston, G.; Prakash, G.; Olah, G. Angew. Chem., Int. Ed. 1998, 37, 820.
      (b) Rudzinski, D. M.; Kelly, C. B.; Leadbeater, N. E. Chem. Commun. 2012, 48, 9610.

    21. [21]

      Chen, W.; Liao, D. Chem. World 2006, 5, 285(in Chinese).  doi: 10.3969/j.issn.0367-6358.2006.05.010

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