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)

Figures(19)

  • 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.
  • 加载中
    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

  • 加载中
    1. [1]

      . 

      CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化

      . CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.

    2. [2]

      Bin XU , Shufeng ZHANG , Feifan LANG , Chunyan NI , Bing WU , Jianping LANG . Photoreactive pyrene-based Zn?? metal-organic frameworks: Solid-state [2+2] cycloaddition and tunable luminescence. Chinese Journal of Inorganic Chemistry, 2026, 42(10): 2119-2126. doi: 10.11862/CJIC.20260140

    3. [3]

      Jiajia Li ,  Xiangyu Zhang ,  Zhihan Yuan ,  Zhengyang Qian ,  Jian Zhu . 3D Printing Based on Photo-Induced Reversible Addition-Fragmentation Chain Transfer Polymerization. University Chemistry, 2024, 39(5): 11-19. doi: 10.3866/PKU.DXHX202309073

    4. [4]

      Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129

    5. [5]

      Yinjie Xu , Suiqin Li , Lihao Liu , Jiahui He , Kai Li , Mengxin Wang , Shuying Zhao , Chun Li , Zhengbin Zhang , Xing Zhong , Jianguo Wang . Enhanced Electrocatalytic Oxidation of Sterols using the Synergistic Effect of NiFe-MOF and Aminoxyl Radicals. Acta Physico-Chimica Sinica, 2024, 40(3): 2305012-0. doi: 10.3866/PKU.WHXB202305012

    6. [6]

      Zhanhui Yang ,  Jiaxi Xu . (m+n+…) or [m+n+…]cycloaddition?. University Chemistry, 2025, 40(3): 387-389. doi: 10.12461/PKU.DXHX202406032

    7. [7]

      Ruolin CHENG , Yue WANG , Xiyao NIU , Huagen LIANG , Ling LIU , Shijian LU . Efficient photothermal catalytic CO2 cycloaddition over W18O49/rGO composites. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1276-1284. doi: 10.11862/CJIC.20240424

    8. [8]

      Lei Shi . Nucleophilicity and Electrophilicity of Radicals. University Chemistry, 2024, 39(11): 131-135. doi: 10.3866/PKU.DXHX202402018

    9. [9]

      Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362

    10. [10]

      Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO2 cycloaddition over W18O49/NH2-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349

    11. [11]

      Tong TAO , Shufeng ZHANG , Feifan LANG , Chunyan NI , Bing WU , Jianping LANG . Synthesis, structures, and daylight-induced [2+2] cycloaddition reactivity of two Cd(Ⅱ)-based pillared-layer coordination polymers. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1121-1130. doi: 10.11862/CJIC.20260115

    12. [12]

      Jinyang SUI , Zhonghao NIU , Hao XU , Jingli XIE . Zinc(Ⅱ) coordination polymers from mixed triazole and carboxylate ligands: Synthesis and properties for CO2 cycloaddition and photocatalytic dye degradation. Chinese Journal of Inorganic Chemistry, 2026, 42(8): 1603-1612. doi: 10.11862/CJIC.20260089

    13. [13]

      Jianjun LI , Mingjie REN , Lili ZHANG , Lingling ZENG , Huiling WANG , Xiangwu MENG . UV-assisted degradation of tetracycline hydrochloride by MnFe2O4@activated carbon activated persulfate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1869-1880. doi: 10.11862/CJIC.20240187

    14. [14]

      Ning CHEN , Jingle CHEN , Hongyuan ZHU , Huali CHEN , Liguang WU , Ting WANG . Mechanism and performance regulation of Co/Zr-doped mesoporous TiO2 catalysts in activating sodium persulfate for tetracycline degradation. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 507-518. doi: 10.11862/CJIC.20250275

    15. [15]

      Tongyan Yu ,  Pan Xu . Visible-Light Photocatalyzed Radical Rearrangement Reaction. University Chemistry, 2025, 40(7): 169-176. doi: 10.12461/PKU.DXHX202409070

    16. [16]

      Xiao Ma ,  Junjie Wang ,  Xin Chen ,  Jingcheng Li ,  Fang Wang ,  Xueping Sun . “我不是坏人!”——一颗自由基的自白书. University Chemistry, 2026, 41(8): 194-202. doi: 10.12461/PKU.DXHX202507008

    17. [17]

      Fa Wang ,  Yu Chen ,  Hui Chao . Ruthenium(II) Complexes as Photoactivated Chemo-Prodrugs for Hypoxic Tumor Therapy. University Chemistry, 2025, 40(7): 200-212. doi: 10.12461/PKU.DXHX202410024

    18. [18]

      Linfeng Zhou ,  Suhao Lin ,  Guodong Sun . Multidimensional Examination of Carbocations. University Chemistry, 2026, 41(6): 467-476. doi: 10.12461/PKU.DXHX202503050

    19. [19]

      Zijian Zhao ,  Yanxin Shi ,  Shicheng Li ,  Wenhong Ruan ,  Fang Zhu ,  Jijun Jiang . A New Exploration of the Preparation of Polyacrylic Acid by Free Radical Polymerization Based on the Concept of Green Chemistry. University Chemistry, 2024, 39(5): 315-324. doi: 10.3866/PKU.DXHX202311094

    20. [20]

      Tao Wen ,  Tao Zhang ,  Changguo Sun ,  Jinyu Liu . Preparation of Dess-Martin Reagent and Its Application in Oxidizing Cyclohexanol. University Chemistry, 2024, 39(5): 20-26. doi: 10.3866/PKU.DXHX202309055

Metrics
  • PDF Downloads(71)
  • Abstract views(6107)
  • HTML views(1954)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return