Citation: Bai Qifan, He Jingyao, Zhu Xiaoqing, Feng Gaofeng, Jin Cheng'an. Visible-Light Mediated Synthesis of 6H-Benzo[c]chromenes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 527-531. doi: 10.6023/cjoc201807058 shu

Visible-Light Mediated Synthesis of 6H-Benzo[c]chromenes

  • Corresponding author: Jin Cheng'an, jca@usx.edu.cn
  • Received Date: 31 July 2018
    Revised Date: 2 September 2018
    Available Online: 12 February 2018

    Fund Project: the Research Project of Shaoxing University 2017LG1001the National Natural Science Foundation of China 21302130Project supported by the National Natural Science Foundation of China (No. 21302130) and the Research Project of Shaoxing University (No. 2017LG1001)

Figures(4)

  • An effective visible-light mediated Ru-catalyzed protocol for accessing 6H-benzo[c]chromenes from benzyloxybenzenediazonium salt via a sequence of dediazoniation, intramolecular radical cyclization and aromaticzation has been developed. The protocol features mild conditions, simple operation and high efficiency, providing a new approach for synthesizing 6H-benzo[c]chromenes.
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    1. [1]

      (a) Evidente, A.; Punzo, B.; Andolfi, A.; Berestetskiy, A.; Motta, A. J. Agric. Food Chem. 2009, 57, 6656.
      (b) Berestetskiy, A.; Cimmino, A.; Sofronova, J.; Dalinova, A.; Avolio, F.; Evidente, M.; Chisty, L.; Krivorotov, D.; Evidente, A. J. Agric. Food Chem. 2015, 63, 1196.

    2. [2]

      Radwan, M. M.; ElSohly, M. A.; Slade, D.; Ahmed, S. A.; Khan, I. A.; Ross, S. A. J. Nat. Prod. 2009, 72, 906.  doi: 10.1021/np900067k

    3. [3]

      Killander, D.; Sterner, O. Eur. J. Org. Chem. 2014, 1594.

    4. [4]

      (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
      (b) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
      (c) Johansson Seechurn, C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 21, 5062.
      (d) Cano, R.; Schmidt, A. F.; McGlacken, G. P. Chem. Sci. 2015, 6, 5338.

    5. [5]

      (a) Majumdar, K. C.; Chakravorty, S.; De, N. Tetrahedron Lett. 2008, 49, 3419.
      (b) Liu, W.; Cao, H.; Xin, J.; Jin, L.; Lei, A. Chem.-Eur. J. 2011, 17, 3588.
      (c) Zhou, J.; Huang, L. Z.; Li, Y. Q.; Du, Z. T. Tetrahedron Lett. 2012, 53, 7036.
      (d) Villamizar, M. C. O.; Zubkov, F. I.; Galvis, C. E. P.; Méndez, L. Y. V.; Kouznetsov, V. V. Org. Chem. Front. 2017, 4, 1736.
      (e) Guo, D. D.; Li, B.; Wang, D. Y.; Gao, Y. R.; Guo, S. H.; Pan, G. F.; Wang, Y. Q. Org. Lett. 2017, 19, 798.
      (f) Cano, R.; Pérez, J. M.; Ramón, D. J.; McGlacken, G. P. Tetrahedron 2016, 72, 1043.
      (g) Sun, C. L.; Gu, Y. F.; Huang, W. P.; Shi, Z. J. Chem. Commun. 2011, 47, 9813.

    6. [6]

      Singha, R.; Ahmed, A.; Nuree, Y.; Ghosh, M.; Ray, J. K. RSC Adv. 2015, 5, 50174.  doi: 10.1039/C5RA07532G

    7. [7]

      He, Y.; Zhang, X.; Cui, L.; Wang, J.; Fan, X. Green Chem. 2012, 14, 3429.  doi: 10.1039/c2gc36379h

    8. [8]

    9. [9]

    10. [10]

      (a) Guo, W.; Lu, L. Q.; Wang, Y.; Wang, Y. N.; Chen, J. R.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 2265.
      (b) Wang, D.; Zhang, L.; Luo, S. Chin. J. Chem. 2018, 36, 311.
      (c) Feng, J.; Li, B.; Jiang, J.; Zhang, M.; Ouyang, W.; Li, C.; Fu, Y.; Gu, Z. Chin. J. Chem. 2018, 36, 11.

    11. [11]

      (a) Kwon, S. J.; Kim, D Y. Org. Lett. 2016, 18, 4562.
      (b) Xue, D.; Jia, Z. H.; Zhao, C. J.; Zhang, Y. Y.; Wang, C.; Xiao, J. Chem.-Eur. J. 2014, 20, 2960.
      (c) Wassmundt, F. W.; Kiesman, W. F. J. Org. Chem. 1996, 60, 196.
      (d) Cano-Yelo, H.; Deronzier, A. J. Chem. Soc., Perkin Trans. 2 1984, 1093.

    12. [12]

      (a) Lee, J. C.; Yuk, J. Y.; Cho, S. H. Synth. Commun. 1995, 25, 1367.
      (b) Maiorana, S.; Baldoli, C.; Licandro, E.; Casiraghi, L.; de Magistris, E.; Paio, A.; Provera, S.; Seneci, P. Tetrahedron Lett. 2000, 41, 7271.
      (c) Schiemann, G.; Winkelmüller, W. Org. Synth. 1933, 13.
      (d) Broxton, T. J.; Bunnett, J. F.; Paik, C. H. J. Org. Chem. 1977, 42, 643.

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