Citation: Liu Lantao, Chen Yingyinga, Zhang An'an, Liu Xue, Zhang Li, Bai Jingru, Li Heng, Mao Guoliang. Palladium Catalyzed Allylic Amination of Cinnamyl Carbonates with Acyl Hydrazones[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 475-481. doi: 10.6023/cjoc201808013 shu

Palladium Catalyzed Allylic Amination of Cinnamyl Carbonates with Acyl Hydrazones

  • Corresponding author: Liu Lantao, liult05@iccas.ac.cn Mao Guoliang, maoguoliang@nepu.edu.cn
  • Received Date: 13 August 2018
    Revised Date: 3 September 2018
    Available Online: 10 February 2018

    Fund Project: the National Natural Science Foundation of China 21572126the Program for Science & Technology Innovation Talents in Universities of Henan Province 14HASTIT016the Program of Science and Technology Innovation Talents of Henan Province 2018JQ0011Project supported by the National Natural Science Foundation of China (No. 21572126), the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 14HASTIT016) and the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011)

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  • Allylic amines moiety exists extensively in natural products, medicines and functional materials. In addition, they are also a kind of versatile building blocks for organic synthesis. Using CH3CN as solvent, the palladium catalyzed allyl amination of cinnamyl carbonate and acylhydrazone compounds was realized under argon. The linear product was formed selectively and the up to 99% yield was obtained. The reaction has features of base free, mild reaction condition, simple operation and broad substrate scope.
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    1. [1]

    2. [2]

    3. [3]

      (a) Monk, J. P.; Brogden, R. N. Drugs 1991, 42, 659.
      (b) Birnbaum, J. E. J. Am. Acad. Dermatol. 1990, 23, 782.
      (c) Xu, Z.; Wang, D. S.; Yu, X.; Yang Y.; Wang, D. Adv. Synth. Catal. 2017, 359, 3332.

    4. [4]

      (a) Stuetz, A.; Petranyi, G. J. Med. Chem. 1984, 27, 1539.
      (b) Rudisill, D. E.; Castonguay, L. A.; Me, J. K. Tetrahedron Lett. 1988, 29, 1509.
      (c) Balfour, J. A.; Fauids, D. Drugs 1992, 43, 259.
      (d) Ge, C.; Sang, X.; Yao, W.; Zhang L.; Wang, D. Green Chem. 2018, 20, 1805.

    5. [5]

      (a) Andersson, P. G.; Backvall, J. E. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.: Negishi, E., Wiley-Interscience, New York, 2002, p. 1859.
      (b) Davies, H. M. L.; Long, M. S. Angew. Chem., Int. Ed. 2005, 44, 3518.
      (c) Jiang, L.; Buchwald, S. L. In Metal-Catalyzed Cross-Coupling Reactions, 2nd ed., Wiley-VCH, Weinheim, 2004, Vol. 2, p. 699.
      (d) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.: Negishi, E., Wiley-Interscience, New York, 2002, p. 1051.

    6. [6]

      (a) Ranerand, K. D.; Ward, A. D. Aust. J. Chem. 1991, 44, 1749.
      (b) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621.
      (c) Vicente, R. Org. Biomol. Chem. 2011, 9, 6469.

    7. [7]

      (a) Schultz, D. M.; Wolfe, J. P. Org. Lett. 2010, 12, 1028.
      (b) Caddick, S.; Koe, W. Tetrahedron Lett. 2002, 43, 9347.
      (c) Sharma, V.; Kumar, P.; Pathak, D. J. Heterocycl. Chem. 2010, 47, 491.
      (d) Lu, T.; Lu, Z.; Ma, Z. X.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2013, 113, 4862.

    8. [8]

      Cho, C. S.; Kim, J. S.; Oh, B. H. Tetrahedron 2000, 56, 7747.  doi: 10.1016/S0040-4020(00)00694-3

    9. [9]

      Cui, X. M. Chlor-Alkali Ind. 2000, 5, 172192(in Chinese).

    10. [10]

    11. [11]

      Lee, O. Y.; Law, K. L.; Yang, D. Org. Lett. 2009, 11, 3302.  doi: 10.1021/ol901111g

    12. [12]

      (a) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364.
      (b) Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2004, 43, 3941.
      (c) Zhou, C. Y.; Zhu, S. F.; Wang, L. X., Zhou, Q. L. J. Am. Chem. Soc. 2010, 132, 10955.
      (d) Holmes, M.; Schwartz, L. A.; Krische, M. J. Chem. Rev. 2018, 118, 6026.

    13. [13]

      (a) Xie, Y. J.; Hu, J. H.; Wang, Y. Y.; Xia, C. G.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
      (b) Liu, Y.; Xie, Y.; Wang, H.; Huang, H. J. Am. Chem. Soc. 2016, 138, 4314.

    14. [14]

      (a) Bäckvall, J. E.; Nordberg, R. E.; Nyström, J. E.; Hoegberg, T.; Ulff, B. J. Org. Chem. 1981, 46, 3479.
      (b) You, S. L.; Zhu, X. Z.; Luo, Y. M.; Hou, X. L.; Dai, L. X. J. Am. Chem. Soc. 2001, 123, 7471.
      (c) Nagano, T.; Kobayashi, S. J. Am. Chem. Soc. 2009, 131, 4200.
      (d) Xie, Y. J.; Hu, J. H.; Wang, Y. Y.; Xia, C.; Huang, H. J. Am. Chem. Soc. 2012, 134, 20613.
      (e) Dubovyk, I.; Watson, I. D. G.; Yudin, A. K. J. Org. Chem. 2013, 78, 1559.
      (f) Cai, A. J.; Guo, W. S.; Martínez-Rodríguez, L.; Kleij, A. W. J. Am. Chem. Soc. 2016, 138, 14194.
      (g) Li, Y. G.; Li, L.; Yang, M. Y.; Kantchev, E. A. B. J. Org. Chem. 2017, 82, 4907.

    15. [15]

      (a) Trost, B. M.; Zhang, T.; Sieber, J. D. Chem. Sci. 2010, 1, 427.
      (b) Evans, P.; Grange, R.; Clizbe, E. Synthesis 2016, 48, 2911.
      (c) Guo, W.; Cai, A.; Xie, J.; Kleij, A. W. Angew. Chem., Int. Ed. 2017, 56, 11797.
      (d) Xia, C.; Shen, J.; Liu, D.; Zhang, W. Org. Lett. 2017, 19, 4251.
      (e) Wang, Y. N.; Wang, B. C.; Zhang, M. M.; Gao, X. W.; Li, T. R.; Lu, L. Q.; Xiao, W. J. Org. Lett. 2017, 19, 4094.

    16. [16]

      Yao, L.; Wang, C. J. Adv. Synth. Catal. 2015, 357, 384.  doi: 10.1002/adsc.201400790

    17. [17]

      Lu, B.; Feng, B.; Ye, H.; Chen, J. R.; Xiao, W. J. Org. Lett. 2018, 20, 3473.  doi: 10.1021/acs.orglett.8b01226

    18. [18]

      Ouyang, K.; Xi, Z. Acta Chim. Sinica 2013, 71, 13(in Chinese).

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