Citation: Teng Qiaoling, Xu Lulu, Cheng Dongping, Xu Xiaoliang. Synthesis of 10-Phenanthrenol Derivatives via Visible Light Catalyzed Itramolecular Cycloaromatization[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4258-4266. doi: 10.6023/cjoc202005077 shu

Synthesis of 10-Phenanthrenol Derivatives via Visible Light Catalyzed Itramolecular Cycloaromatization

  • Corresponding author: Cheng Dongping, chengdp@zjut.edu.cn Xu Xiaoliang, xuxiaoliang@zjut.edu.cn
  • Received Date: 28 May 2020
    Revised Date: 21 July 2020
    Available Online: 5 August 2020

    Fund Project: the National Natural Science Foundation of China 21602197the Zhejiang Provincial Natural Science Foundation LY18B020018Project supported by the Zhejiang Provincial Natural Science Foundation (Nos. LY18B020018, LY15B020004) and the National Natural Science Foundation of China (No. 21602197)the Zhejiang Provincial Natural Science Foundation LY15B020004

Figures(2)

  • Phenanthrene derivatives play an important role in pharmaceutical chemistry and material science. Due to its advantages of green, mild reaction conditions and great application potential, visible light catalysis has become a powerful tool in organic synthesis. In this paper, under the catalysis of photocatalyst Ir[dF(CF3)ppy]2(dtbbpy)PF6, a series of 10-phenanthrenol derivatives were synthesized from 2-arylbenzoyl acetate derivatives in moderate to good yields through intramolecular cycloaromatization. In addition, the plausible reaction mechanism was also proposed.
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    1. [1]

      (a) Floyd, A. J.; Dyke, S. F.; Ward, S. E. Chem. Rev. 1976, 76, 509.
      (b) Kovács, A.; Vasas, A.; Hohmann, J. Phytochemistry 2008, 69, 1084.
      (c) Narita, A.; Wang, X.; Feng, X.; Mullen, K. Chem. Soc. Rev. 2015, 44, 6616.

    2. [2]

      (a) De Alvarenga, M. A.; Gottlieb, O. R.; Magalhaes, M. T. Phytochemistry 1976, 15, 844.
      (b) Pettit, G. R.; Singh, S. B.; Niven, M. L.; Schmidt, J. M. Can. J. Chem. 1988, 66, 406.
      (c) Cragg, G. M.; Newman, D. J. J. Nat. Prod. 2004, 67, 232.

    3. [3]

      (a) Huffman, C. W.; Traxler, J. T.; Krbechek, L. O.; Riter, R. R.; Wagner, R. G. J. Med. Chem. 1971, 14, 90.
      (b) Colwell, W. T.; Brown, V.; Christie, P.; Lange, J.; Reece, C.; Yamamoto, K.; Henry, D. W. J. Med. Chem. 1972, 15, 771.

    4. [4]

      Matsuda, H.; Morikawa, T.; Xie, H.; Yoshikawa, M. Planta Med. 2004, 70, 847.  doi: 10.1055/s-2004-827234

    5. [5]

      (a) Fisch, M. H.; Flick, B. H.; Arditti, J. Phytochemistry 1973, 12, 437.
      (b) Yamaki, M.; Bai, L.; Inoue, K.; Takagi, S. Phytochemistry 1989, 28, 3503.

    6. [6]

      (a) Mitsuhashi, R.; Suzuki, Y.; Yamanari, Y.; Mitamura, H.; Kambe, T.; Ikeda, N.; Okamoto, H.; Fujiwara, A.; Yamaji, M.; Kawasaki, N.; Maniwa, Y.; Kubozono, Y. Nature 2010, 464, 76.
      (b) Lewis, F. D.; Burch, E. L. J. Phys. Chem. 1996, 100, 4055.
      (c) Machado, A. M.; Munaro, M.; Martins, T. D.; Dávila, L. Y. A.; Giro, R.; Caldas, M. J.; Atvars, T. D. Z.; Akcelrud, L. C. Macromolecules 2006, 39, 3398.
      (d) Matsuo, Y.; Sato, Y.; Hashiguchi, M.; Matsuo, K.; Nakamura, E. Adv. Funct. Mater. 2009, 19, 2224.

    7. [7]

      (a) Yadav, A. K.; Ila, J.; Junjappa, H. Eur. J. Org. Chem. 2010, 2010, 338.
      (b) Gupta, V.; Rao, V. U. B.; Das, T.; Vanka, K.; Singh, R. P. J. Org. Chem. 2016, 81, 5663.
      (c) Gupta, V.; Pandey, S. K.; Singh, R. P. Org. Biomol. Chem. 2018, 16, 7134.

    8. [8]

      (a) Bogert, M. T. Science 1933, 77, 289.
      (b) Floyd, A. J.; Dyke, S. F.; Ward, S. E. Chem. Rev. 1976, 76, 509.

    9. [9]

      (a) Almeida, J. F.; Castedo, L.; Fernández, D.; Neo, A. G.; Romero, V.; Tojo, G. Org. Lett. 2003, 5, 4939.
      (b) Kang, Y.; Wang, T.; Liang, Y.; Zhang, Y.; Wang, R.; Zhang, Z. RSC Adv. 2017, 7, 44333.
      (c) Kang, T.; Zhang, W.; Wang, T.; Liang, Y.; Zhang, Z. J. Org. Chem. 2019, 84, 12387.
      (d) Neo, A. G.; López, C.; Romero, V.; Antelo, B.; Delamano, J.; Pérez, A.; Fernandez, D.; Almeida, J. E.; Castedo, L.; Tojo, G. J. Org. Chem. 2010, 75, 6764.

    10. [10]

      (a) Mallory, F. B.; Wood, C. S.; Gordon, J. T. J. Am. Chem. Soc. 1964, 86, 3094.
      (b) Wood, C. S.; Mallory, F. B. J. Org. Chem. 1964, 29, 3373.
      (c) Matsushima, T.; Kobayashi, S.; Watanabe, S. J. Org. Chem. 2016, 81, 7799.

    11. [11]

      Harrowven, D. C.; Nunn, M. I. T.; Fenwick, D. R. Tetrahedron Lett. 2002, 43, 3185.  doi: 10.1016/S0040-4039(02)00505-1

    12. [12]

      Xia, Y.; Liu, Z.; Xiao, Q.; Qu, P.; Ge, R.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2012, 51, 5714.  doi: 10.1002/anie.201201374

    13. [13]

      (a) McMurry, J. E. Acc. Chem. Res. 1983, 16, 405.
      (b) McMurry J. E. Chem. Rev. 1989, 89, 1513.
      (c) Gies, A. E.; Pfeffer, M. J. Org. Chem. 1999, 64, 3650.

    14. [14]

      (a) Iuliano, A.; Piccioli, P.; Fabbri, D. Org. Lett. 2004, 6, 3711.
      (b) Donohoe, T. J.; Orr, A. J.; Bingham, M. Angew. Chem., Int. Ed. 2006, 45, 2664.
      (c) McAtee, C. C.; Riehl, P. S.; Schindler, C. S. J. Am. Chem. Soc. 2017, 139, 2960.

    15. [15]

      Larock, R. C.; Doty, M. J.; Tian, Q.; Zenner, J. M. J. Org. Chem. 1997, 6, 7536.
      (b) Matsumoto, A.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 6557.
      (c) Yan, J.; Yoshikai, N. Org. Lett. 2017, 19, 6630.

    16. [16]

      Gou, B.; Yang, H.; Sun, H.; Chen, J.; Wu, J.; Zhou, L. Org. Lett. 2019, 21, 80.
      (b) Yao, T.; Zhang, H.; Zhao, Y. Org. Lett. 2016, 18, 2532.
      (c) Song, J.; Wang, S.; Sun, H.; Fan, Y.; Xiao, K.; Qian, Y. Org. Biomol. Chem. 2019, 17, 3328.
      (d) Iwasaki, M.; Araki, Y.; Nishihara, Y. J. Org. Chem. 2017, 82, 6242.

    17. [17]

      Liu, Y.; Chen, L.; Wang, Z.; Liu, P.; Liu, Y.; Dai, B. J. Org. Chem. 2019, 84, 204.  doi: 10.1021/acs.joc.8b02605

    18. [18]

      (a) Liu, W.; Zhang, Y.; Guo, H. J. Org. Chem. 2018, 83, 10518.
      (b) Yao, T.; Campo, M. A.; Larock, R. C. J. Org. Chem. 2005, 70, 3511.

    19. [19]

      (a) Xuan, J.; Xiao, W. Angew. Chem., Int. Ed. 2012, 51, 6828.
      (b) Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.
      (c) Dai, C.; Narayanam, J. M. R.; Stephenson, C. R. J. Nat. Chem. 2011, 3, 140.
      (d) Uygur, M.; Danelzik, T.; Mancheño, O. G. Chem. Commun. 2019, 55, 2980.
      (e) Chen, J.; Cen, J.; Xu, X.; Li, X. Catal. Sci. Technol. 2016, 6, 349.
      (f) Chen, Y.; Lu, L.; Yu, D.; Zhu, C.; Xiao, W. Sci. China Chem. 2019, 62, 24.
      (g) Goddard, J. P.; Ollivier, C.; Fensterbank, L. Acc. Chem. Res. 2016, 49, 1924.
      (h) Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527.
      (i) Zhang, H.; Lei, A. Asian J. Org. Chem. 2018, 7, 1164.
      (j) Yu, X.; Zhao, Q.; Chen, J.; Xiao, W.; Chen, J. Acc. Chem Res. 2020, 53, 1066.
      (k) Yang, X.; Guo, J.; Xiao, H.; Feng, K.; Chen, B.; Tung, C.; Wu, L. Angew. Chem. Int. Ed. 2020, 59, 5365.
      (l) Zhang, Q.; Xiong, Q.; Li, M.; Xiong, W.; Shi, B.; Lan, Y.; Lu, L.; Xiao, W. Angew. Chem. Int. Ed. 2020, DOI: 10.1002/anie.202005313

    20. [20]

      Jiang, Y.; Yu, Z.; Zhang, Y.; Wang, B. Org. Lett. 2018, 20, 3728.  doi: 10.1021/acs.orglett.8b01160

    21. [21]

      (a) Dai, X.; Cheng, D.; Guan, B.; Mao, W.; Xu, X.; Li, X. J. Org. Chem. 2014, 79, 7212.
      (b) Dai, X.; Mao, R.; Guan, B.; Xu, X.; Li, X. RSC Adv. 2015, 5, 55290.
      (c) Guan, B.; Xu, X.; Wang, H.; Li, X. Chin. J. Org. Chem. 2016, 36, 1564.
      (d) Ye, Q.; Ye, H.; Cheng, D.; Li, X.; Xu, X. Tetrahedron Lett. 2018, 59, 2546.
      (e) Ye, H.; Ye, Q.; Cheng, D.; Li, X.; Xu, X. Tetrahedron Lett. 2018, 59, 2046.
      (f) Ye, H.; Zhao, H.; Ren, S.; Ye, H.; Cheng, D.; Li, X.; Xu, X. Tetrahedron Lett. 2019, 60, 1302.

    22. [22]

      Becker, P.; Duhamel, T.; Stein, C. J.; Reiher, M.; Muñiz, K. Angew. Chem. Int. Ed. 2017, 56, 8004.  doi: 10.1002/anie.201703611

    23. [23]

      Uyanik, M.; Hayashi, H.; Ishihara, K. Science 2014, 345, 291.  doi: 10.1126/science.1254976

    24. [24]

      (a) Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264.
      (b) Jiang, Y.; Chen, X.; Zheng, Y.; Xue, Z.; Shu, C.; Yuan, W.; Zhang, X. Angew. Chem. Int. Ed. 2011, 50, 7304.

    25. [25]

      Hsiao, Y.; Rivera, N. R.; Rosner, T.; Krska, S. W.; Njolito, E.; Wang, F.; Sun, Y.; Armstrong, J. D.; Grabowski, E. J. J.; Tillyer, R. D.; Spindler, F.; Malan, C. J. Am. Chem. Soc. 2004, 126, 9918.  doi: 10.1021/ja047901i

    26. [26]

      Ji, Y.; Trenkle, W. C.; Vowles, J. V. Org. Lett. 2006, 8, 1161.  doi: 10.1021/ol053164z

    27. [27]

      Jiang, J.; Wang, Y.; Zhang, X. ACS Catal. 2014, 4, 1570.  doi: 10.1021/cs500261k

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