Citation: Hou Wentao, Jia Xiaodong. Recent Progress in Radical Cation Salts Promoted Chemical Transformations[J]. Chinese Journal of Organic Chemistry, ;2018, 38(5): 999-1008. doi: 10.6023/cjoc201711037 shu

Recent Progress in Radical Cation Salts Promoted Chemical Transformations

  • Corresponding author: Jia Xiaodong, jiaxd1975@163.com
  • Received Date: 21 November 2017
    Revised Date: 25 December 2017
    Available Online: 3 May 2018

    Fund Project: the National Natural Science Foundation of China 1362030the National Natural Science Foundation of China 21562038Project supported by the National Natural Science Foundation of China (Nos. 1362030, 21562038)

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  • The first radical cation salt (RCS) was prepared more than 100 years ago, and with the recent renaissance of radical chemistry, the RCS promoted organic transformations attrack extensively attention. In early research, RCS was mainly used to initiate single electron oxidation reactions, such as cycloaddition, fragmentation, rearrangement and so on. Recently, RCS was used to induce the aerobic oxidation of C—H bond, and achieved a series of direct functionalization of C—H bond. In this review, prominent examples from the recent literatures are organized on the basis of the different reactions enabled by RCS catalysis.
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    1. [1]

      (a) Wurster, C. ; Sendtner, R. Ber. Dtsch. Chem. Ges. 1879, 12, 1803.
      (b) Wurster, C. Ber. Dtsch. Chem. Ges. 1879, 12, 2071.

    2. [2]

      (a) Weitz, E. ; Schwechten, H. W. Ber. 1926, 59, 2307.
      (b) Weitz, E. ; Schwechten, H. W. Ber. 1927, 60, 545.

    3. [3]

      (a) Rathore, R. ; Kochi, J. K. J. Org. Chem. 1995, 60, 4399.
      (b) Rathore, R. ; Kochi, J. K. J. Org. Chem. 1995, 60, 7479.
      (c) Debroy, P. ; Shukla, R. ; Lindeman, S. V. ; Rathore, R. J. Org. Chem. 2007, 72, 1765.
      (d) Schneeweis, A. ; Neidlinger, A. ; Reiss, G. J. ; Frank, W. ; Heinze, K. ; Müller T. J. J. Org. Chem. Front. 2017, 4, 839.
      (e) Hiraoka, S. ; Okamoto, T. ; Kozaki, M. ; Shiomi, D. ; Sato, K. ; Takui, T. ; Okada, K. J. Am. Chem. Soc. 2004, 126, 58.
      (f) Chen, X. ; Wang, X. ; Sui, Y. ; Li, Y. ; Ma, J. ; Zuo, J. ; Wang, X. Angew. Chem., Int. Ed. 2012, 51, 11878.

    4. [4]

      (a) Bauld, N. L. ; Pabon, R. J. Am. Chem. Soc. 1983, 105, 633.
      (b) Eberson, L. ; Olofsson, B. Acta Chem. Scand. 1991, 45, 316.

    5. [5]

      Bauld, N. L. Tetrahedron 1989, 45, 5307.  doi: 10.1016/S0040-4020(01)89486-2

    6. [6]

      (a) Schmittel, M. ; von Seggern, H. Angew. Chem., Int. Ed. 1991, 30, 999.
      (b) Schmittel, M. ; von Seggern, H. J. Am. Chem. Soc. 1993, 115, 216.

    7. [7]

      Jia, X.-D.; Lin, H.-C.; Huo, C.-D.; Zhang, W.; Lü, J.-M.; Yang, L.; Zhao, G.-Y.; Liu, Z.-L. Synlett 2003, 1707.

    8. [8]

      (a) Jia, X. -D. ; Han, B. ; Zhang, W. ; Jin, X. -L. ; Yang, L. ; Liu, Z. -L. Synthesis 2006, 2831.
      (b) Jia, X. -D. ; Ren, Y. ; Huo, C. -D. ; Wang, W. -J. ; Chen, X. -N. ; Xu, X. -L. ; Wang, X. -C. Tetrahedron Lett. 2010, 51, 6779.
      (c) Jia, X. -D. ; Qing, C. ; Huo, C. -D. ; Peng, F. -F. ; Wang, X. -C. Tetrahedron Lett. 2012, 53, 7140.
      (d) Jia, X. -D. ; Peng, F. -F. ; Qing, C. ; Huo, C. -D. ; Wang, Y. -X. ; Wang, X. -C. Tetrahedron Lett. 2013, 54, 4950.

    9. [9]

      Takemoto, Y.; Furuse, S.; Koike, H.; Ohra, T.; Iwata, C. Tetrahedron Lett. 1995, 36, 4085.  doi: 10.1016/0040-4039(95)00721-N

    10. [10]

      Huo, C.; Jia, X.; Zhang, W.; Yang, L.; Lü, J.; Liu, Z. Synlett 2004, 251.

    11. [11]

      Huo, C.; Wei, R.; Zhang, W.; Yang, L. Liu, Z. Synlett 2005, 161.
       

    12. [12]

      Huo, C.; Xu, X.; An, J.; Jia, X.; Wang, X.; Wang, C. J. Org. Chem. 2012, 77, 8310.  doi: 10.1021/jo300827s

    13. [13]

      Huo, C.; An, J.; Xu, X.; Jia, X.; Wang, X.; Kang, L. Tetrahedron Lett. 2013, 54, 1145.  doi: 10.1016/j.tetlet.2012.12.078

    14. [14]

      Huo, C.; Kang, L.; Xu, X.; Jia, X.; Wang, X.; Xie, H.; Yuan, Y. Tetrahedron Lett. 2014, 55, 95.
       

    15. [15]

      Li, L.-J.; Jiang, Y.-Y.; Lam, C. M.; Zeng, C.-C.; Hu, L.-M.; Little, R. D. J. Org. Chem. 2015, 80, 11021.  doi: 10.1021/acs.joc.5b02222

    16. [16]

      Marquez, C. A.; Wang, H.; Fabbretti, F.; Metzger, J. O. J. Am. Chem. Soc. 2008, 130, 17208.  doi: 10.1021/ja806791c

    17. [17]

      Huo, C.; Sun, C.; Hua, D.; Jia, X.; Xu, X.; Liu, Z. Tetrahedron Lett. 2011, 52, 7008.  doi: 10.1016/j.tetlet.2011.10.121

    18. [18]

      (a) Adam, W. ; Librera, C. P. J. Org. Chem. 2002, 67, 576.
      (b) Gerken, J. B. ; Wang, S. C. ; Preciado, A. B. ; Park, Y. S. ; Nishiguchi, G. ; Tantillo, D. J. ; Little, R. D. J. Org. Chem. 2005, 70, 4598.
      (c) Park, Y. S. ; Little, R. D. J. Org. Chem. 2008, 73, 6807.

    19. [19]

      Andreu, I.; Delgado, J.; Espinós, A.; Pérez-Ruiz, R.; Jiménez, M. C.; Miranda, M. A. Org. Lett. 2008, 10, 5207.  doi: 10.1021/ol802181u

    20. [20]

      Jia, X.-D.; Peng, F.-F.; Qing, C.; Huo, C.-D.; Wang, X.-C. Org. Lett. 2012, 14, 4030.  doi: 10.1021/ol301909g

    21. [21]

      (a) Jia, X. -D. ; Wang, Y. -X. ; Peng, F. -F. ; Huo, C. -D. ; Yu, L. -L. ; Wang, X. -C. J. Org. Chem. 2013, 78, 9450.
      (b) Wang, Y. -X. ; Peng, F. -F. ; Liu, J. ; Huo, C. -D. ; Wang, X. -C. ; Jia, X. -D. J. Org. Chem. 2015, 80, 609.
      (c) Liu, J. ; Wang, Y. -X. ; Yu, L. -L. ; Huo, C. -D. ; Wang, X. -C. ; Jia, X. -D. Adv. Synth. Catal. 2014, 356, 3214.
      (d) Jia, X. -D. ; Wang, Y. -X. ; Peng, F. -F. ; Huo, C. -D. ; Yu, L. -L. ; Liu, J. ; Wang, X. -C. Adv. Synth. Catal. 2014, 356, 1210.

    22. [22]

      Huo, C.; Wang, C.; Sun, C.; Jia, X.; Wang, X.; Chang, W.; Wu, M. Adv. Synth. Catal. 2013, 355, 1911.  doi: 10.1002/adsc.v355.10

    23. [23]

      Huo, C.; Wang, C.; Wu, M.; Jia, X.; Wang, X.; Yuan, Y.; Xie, H. Org. Biomol. Chem., 2014, 12, 3123.  doi: 10.1039/c3ob42454e

    24. [24]

      Huo, C.; Wu, M.; Jia, X.; Xie, H.; Yuan, Y.; Tang, J. J. Org. Chem. 2014, 79, 9860.  doi: 10.1021/jo5017822

    25. [25]

      Liu, J.; Liu, F.; Zhu, Y.; Ma, X.; Jia, X. Org. Lett. 2015, 17, 1409.  doi: 10.1021/acs.orglett.5b00244

    26. [26]

      Liu, F.; Yu, L.; Lü, S.; Yao, J.; Liu, J.; Jia, X. Adv. Synth. Catal. 2016, 358, 459.  doi: 10.1002/adsc.201500574

    27. [27]

      Jia, X.; Li, P.; Shao, Y.; Yuan, Y.; Hou, W.; Liu, X.; Zhang, X.; Ji, H. Chem. Asian J. 2017, 12, 1719.  doi: 10.1002/asia.v12.14

    28. [28]

      Lü, S.; Zhu, Y.; Ma, X.; Jia, X. Adv. Synth. Catal. 2016, 358, 1004.  doi: 10.1002/adsc.201500885

    29. [29]

      Jia, X.-D.; Lü, S.; Yuan, Y.; Zhang, X.; Zhang, L.; Luo, L. Org. Biomol. Chem., 2017, 15, 2931.  doi: 10.1039/C7OB00446J

    30. [30]

      Jia, X.; Hou, W.; Shao, Y.; Yuan, Y.; Chen, Q.; Li, P.; Liu, X.; Ji, H. Chem. Eur. J. 2017, 23, 12980.  doi: 10.1002/chem.v23.53

    31. [31]

      (a) Huang, L. ; Lin, J. -S. ; Tan, B. ; Liu, X. -Y. ACS Catal. 2015, 5, 2826.
      (b) Qin, Q. ; Yu, S. Org. Lett. 2015, 17, 1894.
      (c) Kundu, R. ; Ball, Z. T. Org. Lett. 2010, 12, 2460.
      (d) Hashimoto, T. ; Hirose, D. ; Taniguchi, T. Angew. Chem., Int. Ed. 2014, 53, 2730.
      (e) Yu, P. ; Lin, J. -S. ; Li, L. ; Zheng, S. -C. ; Xiong, Y. -P. ; Zhao, L. -J. ; Tan, B. ; Liu, X. -Y. Angew. Chem., Int. Ed. 2014, 53, 11890.

    32. [32]

      Jia, X.; Zhu, Y.; Yuan, Y.; Zhang, X.; Lü, S.; Zhang, L.; Luo, L. ACS Catal. 2016, 6, 6033.  doi: 10.1021/acscatal.6b01781

    33. [33]

      (a) Maryanoff, B. E. ; Reitz, A. B. Chem. Rev. 1989, 89, 863.
      (b) Cristau, H. -J. Chem. Rev. 1994, 94, 1299.
      (c) Rein, T. ; Pederson, T. M. Synthesis 2002, 5, 579.
      (d) Hoffmann, R. W. Angew. Chem., Int. Ed. 2001, 40, 1411.

    34. [34]

      Zhu, Y.; Lü, S.; Ma, X.; Zhang, L.; Luo, L.; Jia, X. Asian J. Org. Chem. 2016, 5, 617.  doi: 10.1002/ajoc.201600055

    35. [35]

      Barham, J. P.; John, M. P.; Murphy, J. A. J. Am. Chem. Soc. 2016, 138, 15482.  doi: 10.1021/jacs.6b09690

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