Citation: Guanyu Tao, Feichao Yang, Lujun Zhang, Yang Li, Zheng Duan, François Mathey. Synthesis of phosphanaphthalenes and nido-carborane fused six-membered phosphacycles[J]. Chinese Chemical Letters, ;2021, 32(1): 194-197. doi: 10.1016/j.cclet.2020.11.018 shu

Synthesis of phosphanaphthalenes and nido-carborane fused six-membered phosphacycles

    * Corresponding author.
    E-mail address: duanzheng@zzu.edu.cn (Z. Duan).
  • Received Date: 21 September 2020
    Revised Date: 4 November 2020
    Accepted Date: 9 November 2020
    Available Online: 11 November 2020

Figures(10)

  • A simple method to synthesize luminescent λ5-phosphanaphthalenes and zwitterionic nido-carborane fused six-membered phosphacycles was developed from the reaction of ortho-phosphinobenzoalde-hydes or ortho-phosphinocarboranylaldehydes with an electron-deficient alkyne, respectively. Similar results were obtained with the imino analogues.
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    1. [1]

      P.L. Floch, Coord. Chem. Rev. 250(2006) 627-681.  doi: 10.1016/j.ccr.2005.04.032

    2. [2]

      (a) A. Fukazawa, Y. Sato, T. Higashiyama, et al., Chem. Commun. (Camb.) 52(2016) 1120-1123;
      (b) C. Müller, D. Wasserberg, D. Vogt, et al., Chem. Eur. J. 13(2007) 4548-4559;
      (c) N. Hashimoto, R. Umano, O. Yusuke, et al., J. Am. Chem. Soc. 140(2018) 2046-2049;
      (d) A. Belyaev, Y. Chen, Z. Liu, et al., Chem. Eur. J. 25(2019) 6332-6341;
      (e) W. Ye, X. Li, H. Tian, et al., J. Org. Chem. 85(2020) 3879-3886;
      (f) P. Hindenberg, C. Romero-Nieto, Synlett 27(2016) 2293-2300.

    3. [3]

      (a) E.D. Matveeva, D.S. Vinogradov, N.S. Zefirov, et al., Eur. J. Org. Chem. 2015(2015) 7324-7333;
      (b) E.D. Matveeva, T.A. Podrugina, N.S. Zefirov, et al., J. Org. Chem. 78(2013) 11691-11697;
      (c) E.D. Matveeva, T.A. Podrugina, N.S. Zefirov, et al., Tetrahedron 69(2013) 7395-7402;
      (d) E.D. Matveeva, T.A. Podrugina, N.S. Zefirov, et al., J. Org. Chem. 77(2012) 5770-5774;
      (e) E.D. Matveeva, T.A. Podrugina, N.S. Zefirov, et al., J. Org. Chem. 74(2009) 9428-9432;
      (f) A. Savateev, Y. Vlasenko, N. Shtil, A. Kostyuk, Eur. J. Inorg. Chem. 2016(2016) 628-632.

    4. [4]

      (a) A. Belyaev, Y. Chen, S. Su, I.O. Koshevoy, et al., Chem. Commun. (Camb. ) 53(2017) 10954-10957;
      (b) P. Hindenberg, M. Busch, A. Paul, C. Romero-Nieto, et al., Angew. Chem. Int. Ed. 57(2018) 15157-15161;
      (c) T. Kato, T. Kuwabara, Y. Minami, T. Hiyama, Y. Ishii, Bull. Chem. Soc. Jpn. 92(2019) 1131-1141;
      (d) T. Delouche, A. Vacher, E. Caytan, P.A. Bouit, et al., Chem. Eur. J. 26(2020) 8226-8229.

    5. [5]

      (a) Y.V. Svyaschenko, B.B. Barnych, D.M. Volochnyuk, N.V. Shevchuk, A.N. Kostyuk, J. Org. Chem. 76(2011) 6125-6133;
      (b) Y.V. Svyaschenko, A.N. Kostyuk, B.B. Barnych, D.M. Volochnyuk, Tetrahedron 63(2007) 5656-5664;
      (c) A.N. Kostyuk, Y.V. Svyaschenko, D.M. Volochnyuk, Tetrahedron 61(2005) 9263-6272.

    6. [6]

      K. Dimroth, Delocalized posphorus-carbon double bonds, Heidelberg, Phosphorus-Carbon Double Bonds Fortschritte der Chemischen Forschung, 38/1, Springer, Berlin, 1973, doi: http://dx.doi.org/10.1007/BFb0051365.

    7. [7]

      G. Pfeifer, F. Chahdoura, M. Papke, et al., Chem. Eur. J. 26(2020) 10534-10543.  doi: 10.1002/chem.202000932

    8. [8]

      (a) L. Zhang, W. Yu, C. Liu, et al., Organometallics 34(2015) 5697-5702;
      (b) L. Zhang, F. Yang, G. Tao, et al., Eur. J. Inorg. Chem. 17(2017) 2355-2362;
      (c) H. Huang, Z. Wei, J. Hou, et al., Eur. J. Org. Chem. 22(2018) 2863-2869;
      (d) J. Hou, Y. Xu, Z. Gan, et al., J. Organomet. Chem. 879(2019) 158-161;
      (e) D. Wu, C. Hu, L. Qiu, Z. Duan, F. Mathey, Eur. J. Org. Chem. 37(2019) 6369-6376;
      (f) E. Si, P. Zhao, L. Wang, Z. Duan, F. Mathey, Eur. J. Org. Chem. 6(2020) 697-701.

    9. [9]

      X.F. Zhu, C.E. Henry, O. Kwon, J. Am. Chem. Soc. 129(2007) 6722-6723.  doi: 10.1021/ja071990s

    10. [10]

      A. Bhunia, T. Roy, R.G. Gonnade, A.T. Biju, Org. Lett. 16(2014) 5132-5135.  doi: 10.1021/ol502490t

    11. [11]

      (a) A.R. Popescu, F. Teixidor, C. Viñas, Coord. Chem. Rev. 269(2014) 54-84;
      (b) M. Joost, L. Estévez, K. Miqueu, A. Amgoune, D. Bourissou, Angew. Chem. Int. Ed. 127(2015) 5325-5329;
      (c) Y.O. Wong, M.D. Smith, D.V. Peryshkov, Chem. Eur. J. 22(2016) 6764-6767;
      (d) J.A. Ioppolo, J.K. Clegg, L.M. Rendina, Dalton Trans. 20(2007) 1982-1985;
      (e) C.X. Cui, S. Ren, Z. Qiu, Z. Xie, Dalton Trans. 47(2018) 2453-2459;
      (f) L.E. Riley, A.J. Welch, Claire L. McMullin, et al., Dalton Trans. 46(2017) 5218-5228;
      (g) P. Coburger, E. Hey-Hawkins, et al., Inorg. Chem. 56(2017) 292-304.

    12. [12]

      (a) A. Kreienbrink, M.B. Sárosi, E.G. Rys, P. Lönnecke, E. Hey-Hawkins, Angew. Chem. Int. Ed. 50(2011) 4701-4703;
      (b) A. Kreienbrink, M.B. Sárosi, R. Kuhnert, et al., Chem. Commun. (Camb. ) 51(2015) 836-838;
      (c) J. Schulz, A. Kreienbrink, P. Coburger, et al., Chem. Eur. J. 24(2018) 6208-6216;
      (d) G. Tao, Z. Duan, F. Mathey, Org. Lett. 21(2019) 2273-2276.

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