Citation: Hao Wenyan, Wang Yuyun, Yang Guomin, Liu Yunyun. Nickel-Catalyzed C-H Halogenation of 8-Aminoquinolines for the Synthesis of C(5) and C(7) Di-halogenated Quinolines[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2678-2684. doi: 10.6023/cjoc201704049 shu

Nickel-Catalyzed C-H Halogenation of 8-Aminoquinolines for the Synthesis of C(5) and C(7) Di-halogenated Quinolines

  • Corresponding author: Hao Wenyan, wenyanhao@jxnu.edu.cn Liu Yunyun, chemliuyunyun@jxnu.edu.cn
  • Received Date: 28 April 2017
    Revised Date: 23 June 2017
    Available Online: 4 October 2017

    Fund Project: the Scientific Research Fund of Jiangxi Provincial Education Department GJJ160285the National Natural Science Foundation of China 21762023the National Natural Science Foundation of China 21562024Project supported by the National Natural Science Foundation of China (Nos. 21562024, 21762023) and the Scientific Research Fund of Jiangxi Provincial Education Department (No. GJJ160285)

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  • A simple and efficient nickel-catalyzed oxidative halogenation (Cl, Br) of C(5) and C(7) C-H bond of 8-aminoquinoline amides has been developed. This method employed low-cost and easy availability nickel as catalyst and oxygen as oxidant. The reactions have good functional groups compatibility, giving highly selective C(5) and C(7) di-halogenated products in good to excellent yields.
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    1. [1]

      (a) Kouznetsov, V. V. ; Mendez, L. Y. ; Gomez, C. M. Curr. Org. Chem. 2005, 9, 141.
      (b) Michael, J. P. Nat. Prod. Rep. 2008, 25, 166.
      (c) Tokoro, Y. ; Nagai, A. ; Kokado, K. ; Chujo, Y. Macromolecules 2009, 42, 2988.
      (d) Solomon, V. R. ; Lee, H. Curr. Med. Chem. 2011, 18, 1488.
      (e) Liu, G. ; Yi, M. ; Liu, L. ; Wang, J. ; Wang, J. Chem. Commun. 2015, 51, 2911.

    2. [2]

      (a) Madrid, P. B. ; Sherrill, J. ; Liou, A. P. ; Weisman, J. L. ; Derisi, J. L. ; Guy, R. K. Bioorg. Med. Chem. Lett. 2005, 15, 1015.
      (b) Tardito, S. ; Barilli, A. ; Bassanetti, I. ; Tegoni, M. ; Bussolati, O. ; Franchi-Gazzola, R. ; Mucchino, C. ; Marchio, L. J. Med. Chem. 2012, 55, 10448.
      (c) Abouelhassan, Y. ; Garrison, V. G. ; Burch, M. ; Wong, W. ; Norwood, V. M. ; Huigens, R. W. Bioorg. Med. Chem. Lett. 2014, 24, 5076.
      (d) Vippagunta, S. R. ; Dorn, A. ; Matile, H. ; Bhattacharjee, A. K. ; Karle, J. M. ; Ellis, W. Y. ; Ridley, R. G. ; Vennerstrom, J. L. J. Med. Chem. 1999, 42, 4630.
      (e) Bhat, S. ; Shim, J. S. ; Zhang, F. ; Chong, C. R. ; Liu, J. O. Org. Biomol. Chem. 2012, 10, 2979.
      (f) Borchardt, R. T. J. Med. Chem. 1973, 16, 382.
      (g) Liu, Y. -C. ; Wei, J. -H. ; Chen, Z. -F. ; Liu, M. ; Gu, Y. -Q. ; Huang, K. -B. ; Li, Z. -Q. ; Liang, H. Eur. J. Med. Chem. 2013, 69, 554.

    3. [3]

      (a) Jiang, H. ; Taggart, H. ; Zhang, X. ; Benbrook, D. M. ; Lind, S. E. ; Ding, W. -Q. Cancer Lett. 2011, 312, 11.
      (b) Heidary, D. K. ; Howerton, B. S. ; Glazer, E. C. J. Med. Chem. 2014, 57, 8936.

    4. [4]

      (a) Sun, K. ; Lv, Y. ; Wang, J. ; Sun, J. ; Liu, L. ; Jia, M. ; Liu, X. ; Z. Li, Z. ; Wang, X. ; Org. Lett. 2015, 17, 4408.
      (b) Wasa, M. ; Worrell, B. T. ; Yu, J. Q. Angew. Chem. , Int. Ed. 2010, 49, 1275.
      (c) Tobisu, M. ; Hyodo, I. ; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070.
      (d) Berman, A. M. ; Lewis, J. C. ; Bergman, R. G. ; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926.
      (e) Zhao, D. ; Wang, W. ; Yang, F. ; Lan, J. ; Yang, L. ; Gao, G. ; You, J. Angew. Chem. , Int. Ed. 2009, 48, 3296.

    5. [5]

      (a) Boudet, N. ; Lachs, J. R. ; Knochel, P. Org. Lett. 2007, 9, 5525.
      (b) Kwak, J. ; Kim, M. ; Chang, S. J. Am. Chem. Soc. 2011, 133, 3780.
      (c) Chen, Q. ; du Jourdin, X. M. ; Knochel, P. J. Am. Chem. Soc. 2013, 135, 4958.
      (d) Tsai, C. -C. ; Shih, W. -C. ; Fang, C. -H. ; Li, C. -Y. ; Ong, T. -G. ; Yap, G. P. J. Am. Chem. Soc. 2010, 132, 11887.

    6. [6]

      (a) Guo, H. ; Chen, M. ; Jiang, P. ; Chen, J. ; Pan, L. ; Wang, M. ; Xie, C. ; Zhang, Y. Tetrahedron 2015, 71, 70.
      (b) Xu, J. ; Zhu, X. ; Zhou, G. ; Ying, B. ; Ye, P. ; Su, L. ; Shen, C. ; Zhang, P. Org. Biomol. Chem. 2016, 14, 3016.
      (c) Liu, X. X. ; Wu, Z, Y. ; Luo, X. L. ; He, Y, Q. ; Zhou, X, Q. ; Fan, Y. X. ; Huang. G. S. RSCAdv. 2016, 6, 71485.

    7. [7]

    8. [8]

      For selected example, (a) Zhang, J. ; Chen, T. ; Yang, J. ; Han, L. Chem. Commun. 2015, 51, 7540.
      (b) Li, X. ; Feng, Z. ; Jiang, Z. ; Zhang, X. Org. Lett. 2015, 17, 5570.
      (c) Li, K. ; Wu, Q. ; Lan, J. ; You, J. Nat. Commun. 2015, 6, 8404.
      (d) Jin, L. ; Wan, L. ; Feng, J. ; Cai, C. Org. Lett. 2015, 17, 4726.

    9. [9]

      (a) Cho, C. S. ; Lee, J. W. ; Lee, D. Y. ; Shim, S. C. ; Kim, T. J. Chem. Commun. 1996, 2115.
      (b) Nogi, K. ; Fujihara, T. ; Terao, J. ; Tsuji, Y. J. Org. Chem. 2015, 80, 11618.
      (c) Tjutrins, J. ; Shao, J. ; Yempally, V. ; Bengali, A. A. ; Arndtsen, B. A. Organometallics 2015, 34, 1802.
      (d) Lo, W. ; Hu, C. ; Berenson, T. ; Tracer, N. ; Shlian, D. ; Khaloo, M. ; Benhaim, A. ; Jiang, J. Chem. Commun. 2015, 51, 9432.
      (e) Hoshimoto, Y. ; Ohata, T. ; Sasaoka, Y. ; Ohashi, M. ; Ogoshi, S. J. Am. Chem. Soc. 2014, 136, 15877.

    10. [10]

      (a) Ohashi, M. ; Kishizaki, O. ; Ikeda, H. ; Ogoshi, S. J. Am. Chem. Soc. 2009, 131, 9160.
      (b) Sato, Y. ; Saito, N. ; Mori, M. J. Am. Chem. Soc. 2000, 122, 2371.
      (c) Yeh, C. H. ; Korivi, R. P. ; Cheng, C. H. Angew. Chem. , Int. Ed. 2008, 47, 4892.
      (d) Stolley, R. M. ; Duong, H. A. ; Thomas, D. R. ; Louie, J. J. Am. Chem. Soc. 2012, 134, 15154.
      (e) Thakur, A. ; Facer, M. E. ; Louie, J. Angew. Chem. , Int. Ed. 2013, 52, 12161.

    11. [11]

      Zhan, B.-B.; Liu, Y.-H.; Hu, F.; Shi, B.-F. Chem. Commun. 2016, 52, 4934.  doi: 10.1039/C6CC00822D

    12. [12]

      (a) Hao, W. Y. ; Tian, J. ; Li, W. ; Shi, R. ; Huang, Z. ; Lei. A. W. Chem. Asian J. 2016, 11, 1664.
      (b) Wan, J. -P. ; Li, Y. ; Liu, Y. Org. Chem. Front. 2016, 3, 768.
      (c) Liu, Y. ; Huang, M. ; Wei, L. Asian J. Org. Chem. 2017, 6, 41.

    13. [13]

      He, Y.; Zhao, N.; Qiu, L.; Zhang, X.; Fan, X. Org. Lett. 2016, 18, 6054.  doi: 10.1021/acs.orglett.6b02998

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