Citation: Zhao Suyan, Wang Zuli. Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst[J]. Chinese Journal of Organic Chemistry, ;2016, 36(4): 862-866. doi: 10.6023/cjoc201510027 shu

Synthesis of Phenols under Mild Conditions in Water Using Recyclable Chitosan@Copper as Catalyst

  • Corresponding author: Wang Zuli, 
  • Received Date: 23 October 2015
    Available Online: 16 November 2015

    Fund Project: 国家自然科学基金(No.21402103) (No.21402103)山东省优秀中青年基金(No.BS2013YY024) (No.BS2013YY024)中国博士后基金(No.150030)资助项目. (No.150030)

  • A green and efficient protocol for the synthesis of phenols using recyclable chitosan@copper as catalyst was developed. Phenols can be obtained in moderate to excellent yields. The catalyst can be recycled and reused for five times without significant loss of its catalytic activity.
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    1. [1]

      [1] Rappoport, Z. The Chemistry of Phenols, Wiley-VCH, Weinheim,Germany, 2003.

    2. [2]

      [2] Zhang, R. X.; Zhang, X. D. Chemical Industry 2008, 26, 47 (in Chinese). (张日新, 张晓东, 化学工业, 2008, 26, 47.)

    3. [3]

      [3] (a) Anderson, K. W.; Ikawa, T. R.; Tundel, E. S.; Buchwald, L. J. Am. Chem. Soc.2006, 128, 10694.

    4. [4]

      (b) Willis, M. C. Angew. Chem., Int. Ed. 2007, 46, 3402.

    5. [5]

      (c) Sergeev, A. G.; Schulz, T.; Torborg, C.; Spannenberg, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 7595.

    6. [6]

      (d) Schulz, T.; Torborg, C.; Schäffner, B.; Huang, J.; Zapf, A.; Kadyrov, R.; Börner, A.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 918.

    7. [7]

      (e) Gallon, B. J.; Kojima, R. W.; Kaner, R. B.; Diaconescu, P. L. Angew. Chem., Int. Ed. 2007, 46, 7251.

    8. [8]

      (f) Chen, G. S.; Chan, A. S. C.; Kwong, F. Y. Tetrahedron Lett. 2007, 48, 473.

    9. [9]

      [4] (a) Yang, D. S.; Fu, H. Chem. Eur. J. 2010, 16, 2366.

    10. [10]

      (b) Kormos, C. M.; Leadbeater, N. E. Tetrahedron 2006, 62, 4728;

    11. [11]

      (c) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.

    12. [12]

      (d) Zhao, D. B.; Wu, N. J.; Zhang, S.; Xi, P.; Su, X. Y.; Lan, J. B.; You, J. S. Angew. Chem., Int. Ed. 2009, 48, 8729.

    13. [13]

      [5] Yin, L.; Leibescher, J. Chem. Rev. 2007, 107, 133.

    14. [14]

      [6] Li, B.; Li, M.; Yao, C. H.; Shi, Y. F.; Ye, D. R.; Wu, J.; Zhao, D. Y. J. Mater. Chem. 2013, 1, 6742.

    15. [15]

      [7] For selected examples, see: (a) Kantam, M. L.; Yadav, Y.; Laha, Y.; Srinivas, P.; Sreedhar, B.; Figueras, F. J. Org. Chem. 2009, 74, 4608.

    16. [16]

      (b) Kundu, D.; Chatterjee, T.; Ranu, B. C. Adv. Synth. Catal. 2013, 355, 2285.

    17. [17]

      (c) Brahmachari, G.; Laskar, S.; Barik, P. RSC Adv. 2013, 3, 142;

    18. [18]

      (d) Parella, R.; Kumar, A; Babu, S. A. Tetrahedron Lett. 2013, 54, 1738.

    19. [19]

      (e) Yang, S.; Wu, C.; Zhou, H.; Yang, Y.; Zhao, Y.; Wang, C.; Yang, W.; Xu, J. Adv. Synth. Catal. 2013, 355, 53.

    20. [20]

      (f) Swapna, K.; Murthy, S. N.; Jyothi, M. T.; Nageswar, Y. V. D. Org. Biomol. Chem. 2011, 5989.

    21. [21]

      (g) Hudson, R.; Ishikawa, S.; Li, C.-J.; Moores, A. Synlett 2013, 1637.

    22. [22]

      (h) Dandia, A.; Jain, A. K.; Sharma, S. RSC Adv. 2013, 3, 2924.

    23. [23]

      (i) Kumar, A. S.; Reddy, M.; M.Knorn, A.; Reiser, O.; Sreedhar, B. Eur. J. Org. Chem. 2013, 4, 674.

    24. [24]

      (j) Wang, Z. L. RSC Adv. 2015, 5, 5563.

    25. [25]

      [8] Zhang, J.; Han, D.; Zhang, H.; Chaker, M.; Zhao, Y.; Ma, D. Chem. Commun. 2012, 48, 11510.

    26. [26]

      [9] (a) Makhubela, B. C. E.; Jardine, A.; Smith, G. S. Appl. Catal. 2011, 393, 231.

    27. [27]

      (b) Lasri, J.; Leod, T. C. O. M.; Pombeiro, A. J. L. Appl. Catal. 2011, 393, 94.

    28. [28]

      (c) Yi, S. S.; Lee, D. H.; Sin, E.; Lee, Y. S. Tetrahedron Lett. 2007, 48, 6771.

    29. [29]

      [10] (a) Shen, C.; Xu, J.; Yu, W.; Zhang, P. Green Chem. 2014, 16, 3007.

    30. [30]

      (b) Shen, C.; Xu, J.; Yu, W. B.; Zhang, P. F. Green Chem. 2014, 16, 3007.

    31. [31]

      [11] Yang, B.; Mao, Z. X.; Zhu, X. H.; Wan, Y. Q. Catal. Commun. 2015, 60, 92.

    32. [32]

      [12] Pal, M.; Parasuraman, K.; Yeleswarapu, K. R. Org. Lett. 2003, 5, 349.

    33. [33]

      [13] Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2011, 76, 623.

    34. [34]

      [14] Jiang, M.; Yang, H. J.; Li, Y.; Jia, Z. Y.; Fu, H. Chin. Chem. Lett. 2014, 25, 715.

    35. [35]

      [15] Yang, D. S.; An, B. J.; Wei, W.; Jiang, M.; You, J. M.; Wang, H. Tetrahedron 2014, 70, 3630.

    36. [36]

      [16] Xu, J. M.; Wang, X. Y.; Shao, C. W.; Su, D. Y.; Cheng, G. L.; Hu, Y. F. Org. Lett. 2010, 12, 164.

    37. [37]

      [17] Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 8725.

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