Citation: Yang Qi, Liu Liang, Zhang Wen-Xiong, Xi Zhenfeng. Gold(Ⅰ)-Catalyzed 1, 2-Migration of a SiMe3 Group on Naphthalene Rings[J]. Chinese Journal of Organic Chemistry, ;2018, 38(1): 272-276. doi: 10.6023/cjoc201708059 shu

Gold(Ⅰ)-Catalyzed 1, 2-Migration of a SiMe3 Group on Naphthalene Rings

  • Corresponding author: Xi Zhenfeng, zfxi@pku.edu.cn
  • Received Date: 29 August 2017
    Revised Date: 19 September 2017
    Available Online: 19 January 2017

    Fund Project: the National Natural Science Foundation of China 21690061Project supported by the National Natural Science Foundation of China (Nos. 21372012, 21690061)the National Natural Science Foundation of China 21372012

Figures(3)

  • A gold(Ⅰ)-catalyzed 1, 2-silyl migration on 1, 8-di-substituted naphthalene rings was realized by synergistic effect of Lewis acid and water. High yields were achieved under relatively mild conditions.
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    1. [1]

      (a) Weber, W. P. Silicon Reagents in Organic Synthesis, Springer, V., Berlin, 1983.
      (b) Pati, S. In the Chemistry of Organic Silicon Compounds, Vol. 2, Eds.: Rappoport, Z.; Apeloin, Y., Wiley, Chichester, U. K., 1998.
      (c) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley, New York, 2000.

    2. [2]

      For reviews, see:
      (a) Brook, A. G. Acc. Chem. Res. 1974, 7, 77.
      (b) Moser, W. H. Tetrahedron 2001, 57, 2065.
      (c) Smith Ⅲ, A. B.; Adams, C. M. Acc. Chem. Res. 2004, 37, 365.
      (d) Smith Ⅲ, A. B.; Wuest, W. M. Chem. Commun. 2008, 44, 5883.

    3. [3]

    4. [4]

      For reviews on transition-metal catalyzed cleavage of C(sp3)—Si bonds, see:
      (a) Wang, L.; Duan, Z. Chin. Sci. Bull. 2013, 58, 307.
      (b) Zhang, Q.; An, K.; He, W. Synlett 2015, 26, 1145.
      (c) Li, L.; Zhang, Y.; Gao, L.; Song, L. Tetrahedron Lett. 2015, 56, 1466.
      (d) Komiyama, K.; Minami, Y.; Hiyama, T. ACS Catal. 2017, 7, 631.

    5. [5]

      (a) Seyferth, D.; White, D. L. J. Am. Chem. Soc. 1972, 94, 3132.
      (b) Seyferth, D.; White, D. L. J. Organomet. Chem. 1972, 34, 119.
      (c) Hillurd Ⅲ, R. L.; Vollharrt, K. P. C. Angew. Chem., Int. Ed. 1975, 14, 712.

    6. [6]

      Soorlyakumaran, R.; Boudjouk, P. Organometallics 1982, 1, 219.  doi: 10.1021/om00061a040

    7. [7]

      (a) Anderson, J. E.; Franck, R. W.; Mandella, W. L. J. Am. Chem. Soc. 1972, 94, 1278.
      (b) Seyferth, D.; Vick, S. C. J. Organomet. Chem. 1977, 141, 173.
      (c) Cozzi, F.; Sjö strand, U.; Mislow, K. J. Organomet. Chem. 1979, 174, C1.
      (d) Hutchings, M. G.; Watt, I. J. Organomet. Chem. 1979, 177, 329.
      (e) Wrocynski, R. J.; Baum, M. W.; Kost. D.; Mislow, K.; Vick, S. C.; Seyferth, D. J. Organomet. Chem. 1979, 170, C29.
      (f) Kiely, J. S.; Boudjouk, P. J. Organomet. Chem. 1979, 182, 173.
      (g) Anet, F. A. L.; Donovan, D.; Sjö strand, U.; Mislow, K. J. Am. Chem. Soc. 1980, 102, 1748.
      (h) Blount, J. F.; Cozzi, F.; Damewood, J. R. Jr.; Iroff, L. D.; Sjö strand, U.; Mislow, K. J. Am. Chem. Soc. 1980, 102, 99.

    8. [8]

    9. [9]

      Xi, Z. Sci. China, Ser. B:Chem. 2009, 39, 1115(in Chinese).

    10. [10]

      (a) Olah, G. A.; Meyer, W.; Overchuk, N. A. J. Org. Chem. 1964, 29, 2313.
      (b) Olah, G. A.; Meyer, W.; Overchuk, N. A. J. Org. Chem. 1964, 29, 2315.
      (c) Dudnik, A. S.; Xia, Y.; Li, Y.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 764.
      (d) Chen, M.; Sun, N.; Xu, W.; Zhao, J.; Wang, G.; Liu, Y. Chem.-Eur. J. 2015, 21, 18571.

    11. [11]

      Sun, F.; Gu, Z. Org. Lett. 2015, 17, 2222.  doi: 10.1021/acs.orglett.5b00830

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