Citation: Zhao Jingfeng, Duan Xinhua, Guo Li'na. Recent Advances in Persulfates-Promoted Radical Reaction[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2498-2511. doi: 10.6023/cjoc201705003 shu

Recent Advances in Persulfates-Promoted Radical Reaction

  • Corresponding author: Guo Li'na, guoln81@xjtu.edu.cn
  • Received Date: 2 May 2017
    Revised Date: 22 June 2017
    Available Online: 4 October 2017

    Fund Project: the Natural Science Basic Research Plan in Shaanxi Province 2016JZ002Project supported by the Natural Science Basic Research Plan in Shaanxi Province (No. 2016JZ002).

Figures(16)

  • As cheap, environmentally friendly, easily handled strong oxidants, persulfates have been widely used in organic synthesis. It is well known that persulfates may decompose to sulfate radical anions (SO4) under heating, light irradiation or transition-metal reductive conditions. Studies indicate that the sulfate radical anion is a powerful single-electron oxidant, which can oxidize a variety of neutral molecules and anions to give the corresponding radicals. The new generated radicals can further undergo a series of chemical transformations to provide structurally diverse and useful compounds. Recent radical reactions promoted by persulfates are summarized. The full text contains five parts. In the first and second parts, recent advance in the radical cyclization reactions and functionalization of C-H bonds promoted by persulfates is discussed. The third part introduced the persulfates-mediated photocatalytic reactions. The fourth part emphasized persulfates-promoted other free radical reactions. Finally, some perspectives on the future development of this chemistry are given.
  • 加载中
    1. [1]

      (a) Recupero, F.; Punta, C. Chem. Rev. 2007, 107, 3800.
      (b) Zard, S. Z. Chem. Soc. Rev. 2008, 37, 1603.
      (c) Wille, U. Chem. Rev. 2013, 113, 813.
      (d) Hoffmann, R. W. Chem. Soc. Rev. 2016, 45, 577.
      (e) Staveness, D.; Bosque, I.; Stephenson, C. R. J. Acc. Chem. Res. 2016, 49, 2295.
      (f) Matcha, K.; Narayan, R.; Antonchick, A. P. Angew. Chem., Int. Ed. 2013, 52, 7985.
      (g) Tang, S.; Liu, K.; Liu, C.; Lei, A.-W. Chem. Soc. Rev. 2015, 44, 1070.

    2. [2]

      (a) Caron, S.; Dugger, R. W.; Ruggeri, S. G.; Ragan, J. A.; Ripin, D. H. B. Chem. Rev. 2006, 106, 2943.
      (b) Xu, G.; Chance, M. R. Chem. Rev. 2007, 107, 3514.
      (c) Nicolaou, K. C.; Chen, J. S. Chem. Soc. Rev. 2009, 38, 2993.
      (d) Yu, L.-F.; Hu, H.-N.; Nan, F.-J. J. Org. Chem. 2011, 76, 1448.
      (e) Yin, J.; Kong, L.-L.; Gao, S.-H. Chin. J. Org. Chem. 2013, 33, 259(in Chinese).
      (尹军, 孔丽丽, 高栓虎, 有机化学, 2013, 33, 259.)
      (f) Newcomb, E. T.; Knutson, P. C.; Pedersen, B. A.; Ferreira, E. M. J. Am. Chem. Soc. 2016, 138, 108.

    3. [3]

      (a) Satoh, K.; Kamigaito, M. Chem. Rev. 2009, 109, 5120.
      (b) Ratera, I.; Veciana, J. Chem. Soc. Rev. 2012, 41, 303.
      (c) Tzirakis, M. D.; Orfanopoulos, M. Chem. Rev. 2013, 113, 5262.
      (d) Zhang, N.; Samanta, S. R.; Rosen, B. M.; Percec, V. Chem. Rev. 2014, 114, 5848.

    4. [4]

      For selected reviews, see:
      (a) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
      (b) Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170.
      (c) Enthaler, S.; Company, A. Chem. Soc. Rev. 2011, 40, 4912.
      (d) Sun, M.; Zhang, J.; Putaj, P.; Caps, V.; Lefebvre, F.; Pelletier, J.; Basset, J.-M. Chem. Rev. 2014, 114, 981.
      (e) Xia, Y.; Wang, J. Chem. Soc. Rev. 2017, 46, 2306.

    5. [5]

      (a) Liang, C.-J.; Bruell, C. J.; Marley, M. C.; Sperry, K. L. Soil Sediment Contam. 2003, 12, 207.
      (b) House, D. A. Chem. Rev. 1962, 62, 185.
      (c) Liang, C.-J.; Bruell, C. J.; Marley, M. C.; Sperry, K. L. Chemosphere 2004, 55, 1225.
      (d) Wang, Y.-B.; Hong, C.-S. Water. Res. 1999, 33, 2031.

    6. [6]

      (a) Minisci, F.; Bernardi, R.; Bertini, F.; Galli, R.; Perchinummo, M. Tetrahedron 1971, 27, 3575.
      (b) Minisci, F.; Galli, R.; Cecere, M.; Malatesta, V.; Caronna, T. Tetrahedron Lett. 1968, 9, 5609.
      (c) Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489.

    7. [7]

      (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795.
      (b) Wong, H. N. C.; Yu, P.; Yick, C. Y. Pure Appl. Chem. 1999, 71, 1041.
      (c) Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Chem. Soc. Rev. 2000, 29, 109.
      (d) Chinchilla, R.; Najera, C.; Yus, M. Chem. Rev. 2004, 104, 2667.
      (e) Lee, H.-K.; Chan, K.-F.; Hui, C.-W.; Yim, H.-K.; Wu, X.-W.; Wong, H. N. C. Pure Appl. Chem. 2005, 77, 139.

    8. [8]

      (a) Chen, J.-R.; Yu, X.-Y.; Wen, J. Synthesis 2015, 47, 604.
      (b) Song, R.-J.; Liu, Y.; Xie, Y.-X.; Li, J.-H. Synthesis 2015, 47, 1195.
      (c) Li, C.-C.; Yang, S.-D. Org. Biomol. Chem. 2016, 14, 4365.
      (d) Li, Y.-M.; Wei, X.-H.; Li, X.-A.; Yang, S.-D. Chem. Commun. 2013, 49, 11701.
      (e) Qiu, J.; Zhang, R.-H. Org. Biomol. Chem. 2014, 12, 4329.

    9. [9]

      (a) Wang, H.; Guo, L.-N.; Duan, X.-H. Chem. Commun. 2013, 49, 10370.
      (b) Wang, H.; Guo, L.-N.; Duan, X.-H. Org. Lett. 2013, 15, 5254.

    10. [10]

      (a) Yin, F.; Wang, X.-S. Org. Lett. 2014, 16, 1128.
      (b) Wei, W.; Wen, J.-W.; Yang, D.-S.; Liu, X.-X.; Guo, M.-Y.; Dong, R.-M.; Wang, H. J. Org. Chem. 2014, 79, 4225.

    11. [11]

      (a) Wei, W.; Wen, J.-W.; Yang, D.-S.; Du, J.; You, J.-M.; Wang, H. Green Chem. 2014, 16, 2988.
      (b) Zhang, M.-Z.; Ji, P.-Y.; Liu, Y.-F.; Xu, J.-W.; Guo, C.-C. Adv. Synth. Catal. 2016, 358, 2976.

    12. [12]

      (a) Li, Y.-M.; Sun, M.; Wang, H.-L.; Tian, Q.-P.; Yang, S.-D. Angew. Chem., Int. Ed. 2013, 52, 3972.
      (b) Li, Y.-M.; Shen, Y.-H.; Chang, K.-J.; Yang, S.-D. Tetrahedron 2014, 70, 1991(in Chinese).

    13. [13]

      (a) Guo, L.-N.; Deng, Z.-Q.; Wu, Y.; Hu, J. RSC Adv. 2016, 6, 27000.
      (b) Li, Y.-H.; Wang, J.-J.; Wei, X.-H.; Yang, S.-D. Chin. J. Org. Chem. 2015, 35, 638(in Chinese).
      (李永红, 王君姣, 魏小红, 杨尚东, 有机化学, 2015, 35, 638.)

    14. [14]

      (a) Laha, J. K.; Tummalapalli, K. S. S.; Gupta. A. Org. Lett. 2014, 16, 4392.
      (b) Laha, J. K.; Tummalapalli, K. S. S.; Nair, A.; Patel, N. J. Org. Chem. 2015, 80, 11351.
      (c) Laha, J. K.; Patel, K. V.; Tummalapalli, K. S. S.; Dayal, N. Chem. Commun. 2016, 52, 10245.

    15. [15]

      Wang, S.; He, L.-Y.; Guo, L.-N. Synthesis 2015, 47, 3191.  doi: 10.1055/s-00000084

    16. [16]

      (a) Yang, H.; Duan, X.-H.; Zhao, J.-F.; Guo, L.-N. Org. Lett. 2015, 17, 1998.
      (b) Guo, L.-N.; Gu, Y.-R.; Yang, H.; Hu, J. Org. Biomol. Chem. 2016, 14, 3098.

    17. [17]

      Gao, P.; Wang, J.; Bai, Z.-J.; Shen, L.; Yan, Y.-Y.; Yang, D.-S.; Fan, M.-J.; Guan, Z.-H. Org. Lett. 2016, 18, 6074.  doi: 10.1021/acs.orglett.6b03060

    18. [18]

      Chen, M.-T.; Tang, X.-Y.; Shi, M. Org. Chem. Front. 2017, 4, 86.  doi: 10.1039/C6QO00536E

    19. [19]

      Liu, Y.-K.; Jiang, B.; Zhang, W.; Xu, Z.-Y. J. Org. Chem. 2013, 78, 966.  doi: 10.1021/jo302450f

    20. [20]

      (a) Shi, Z.-Z.; Glorius, F. Chem. Sci. 2013, 4, 829.
      (b) Siddaraju, Y.; Lamani, M.; Prabhu, K. R. J. Org. Chem. 2014, 79, 3856.

    21. [21]

      (a) More, N. Y.; Jeganmohan, M. Org. Lett. 2014, 16, 804.
      (b) More, N. Y.; Jeganmohan, M. Org. Lett. 2015, 17, 3042.

    22. [22]

      (a) Fujiwara, Y.; Domingo, V.; Seiple, I. B.; Gianatassio, R.; Bel, M. D.; Baran, P. S. J. Am. Chem. Soc. 2011, 133, 3292.
      (b) Ilangovan, A.; Polu, A.; Satish, G. Org. Chem. Front. 2015, 2, 1616.

    23. [23]

      (a) Wang, D.-G.; Deng, G.-J.; Chen, S.-Y.; Gong, H. Green Chem. 2016, 18, 5967.
      (b) Mete, T. B.; Khopade, T. M.; Bhat, R. G. Tetrahedron Lett. 2017, 58, 415.

    24. [24]

      (a) Yang, D.-S.; Yan, K.-L.; Wei, W.; Li, G.-Q.; Lu, S.-L.; Zhao, C.-X.; Tian, L.-J.; Wang, H. J. Org. Chem. 2015, 80, 11073.
      (b) Yan, K.-L.; Yang, D.-S.; Wei, W.; Zhao, J.; Shuai, Y.-Y.; Tian, L.-J.; Wang, H. Org. Biomol. Chem. 2015, 13, 7323.

    25. [25]

      (a) Li, X.; Che, X.; Chen, G.-H.; Zhang, J.; Yan, J.-L.; Zhang, Y.-F.; Zhang, L.-S.; Hsu, C.-P.; Gao, Y.-Q.; Shi, Z.-J. Org. Lett. 2016, 18, 1234.
      (b) Li, X.; Shi, Z.-J. Org. Chem. Front. 2016, 3, 1326.
      (c) Yuan, G.-Y.; Wang, F.; Stephenson, N. A.; Wang, L.; Rotstein, B. H.; Vasdev, N.; Tang, P.-P.; Liang, S. H. Chem. Commun. 2017, 53, 126.
      (d) Kumar, P.; Guntreddi, T.; Singh, R.; Singh, K. N. Org. Chem. Front. 2017, 4, 147.

    26. [26]

      (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
      (b) Ravelli, D.; Protti, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850.
      (c) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828.

    27. [27]

      (a) Devari, S.; Shah, B.-A. Chem. Commun. 2016, 52, 1490.
      (b) Zhang, Y.-Q.; Teuscher, K. B.; Ji, H.-T. Chem. Sci. 2016, 7, 2111.

    28. [28]

      (a) Zhao, Y.-T.; Huang, B.-B.; Yang, C.; Xia, W.-J. Org. Lett. 2016, 18, 3326.
      (b) Meyer, A. U.; Alexander, W.; König, B. Angew. Chem., Int. Ed. 2017, 56, 409.

    29. [29]

      (a) Guo, L.-N.; Wang, H.; Duan, X.-H. Org. Biomol. Chem. 2016, 14, 7380.
      (b) Wang, H.; Guo, L.-N.; Wang, S.; Duan, X.-H. Org. Lett. 2015, 17, 3054.
      (c) Wang, P.-F.; Feng, Y.-S.; Cheng, Z.-F. J. Org. Chem. 2015, 80, 9314.
      (d) Wang, S.; Guo, L.-N.; Wang, H.; Duan, X.-H. Org. Lett. 2015, 17, 4798.

    30. [30]

      (a) Nishimura, T.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 2645.
      (b) Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 1999, 121, 11010.

    31. [31]

      Sun, K.; Wang, X.; Lv, Y.-H.; Li, G.; Jiao, H.-Z.; Dai, C.-W.; Li, Y.-Y.; Zhang, C.; Liu, L. Chem. Commun. 2016, 52, 8471.  doi: 10.1039/C6CC04225B

  • 加载中
    1. [1]

      Jianjun LIMingjie RENLili ZHANGLingling ZENGHuiling WANGXiangwu 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

    2. [2]

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

    3. [3]

      Danqing Wu Jiajun Liu Tianyu Li Dazhen Xu Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087

    4. [4]

      Min LIUHuapeng RUANZhongtao FENGXue DONGHaiyan CUIXinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362

    5. [5]

      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

    6. [6]

      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

    7. [7]

      Jinyao Du Xingchao Zang Ningning Xu Yongjun Liu Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039

    8. [8]

      Xinyu Zhu Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106

    9. [9]

      Chengqian Mao Yanghan Chen Haotong Bai Junru Huang Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014

    10. [10]

      Jihua Deng Xinshi Wu Dichang Zhong . Exploration of Green Teaching and Ideological and Political Education in Chemical Experiment of “Preparation of Ammonium Ferrous Sulfate”. University Chemistry, 2024, 39(10): 325-329. doi: 10.12461/PKU.DXHX202405046

    11. [11]

      Yinuo Wang Siran Wang Yilong Zhao Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063

    12. [12]

      Jiapei Zou Junyang Zhang Xuming Wu Cong Wei Simin Fang Yuxi Wang . A Comprehensive Experiment Based on Electrocatalytic Nitrate Reduction into Ammonia: Synthesis, Characterization, Performance Exploration, and Applicable Design of Copper-based Catalysts. University Chemistry, 2024, 39(6): 373-382. doi: 10.3866/PKU.DXHX202312081

    13. [13]

      Jie ZHAOHuili ZHANGXiaoqing LUZhaojie WANG . Theoretical calculations of CO2 capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213

    14. [14]

      Yuyao Wang Zhitao Cao Zeyu Du Xinxin Cao Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-. doi: 10.3866/PKU.WHXB202406014

    15. [15]

      Yixuan Gao Lingxing Zan Wenlin Zhang Qingbo Wei . Comprehensive Innovation Experiment: Preparation and Characterization of Carbon-based Perovskite Solar Cells. University Chemistry, 2024, 39(4): 178-183. doi: 10.3866/PKU.DXHX202311091

    16. [16]

      Shiyan Cheng Yonghong Ruan Lei Gong Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024

    17. [17]

      Doudou Qin Junyang Ding Chu Liang Qian Liu Ligang Feng Yang Luo Guangzhi Hu Jun Luo Xijun Liu . Addressing Challenges and Enhancing Performance of Manganese-based Cathode Materials in Aqueous Zinc-Ion Batteries. Acta Physico-Chimica Sinica, 2024, 40(10): 2310034-. doi: 10.3866/PKU.WHXB202310034

    18. [18]

      Yu Guo Zhiwei Huang Yuqing Hu Junzhe Li Jie Xu . 钠离子电池中铁基异质结构负极材料的最新研究进展. Acta Physico-Chimica Sinica, 2025, 41(3): 2311015-. doi: 10.3866/PKU.WHXB202311015

    19. [19]

      Yi DINGPeiyu LIAOJianhua JIAMingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393

    20. [20]

      Lina Guo Ruizhe Li Chuang Sun Xiaoli Luo Yiqiu Shi Hong Yuan Shuxin Ouyang Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al2O3催化剂光热催化CO2甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002

Metrics
  • PDF Downloads(629)
  • Abstract views(25468)
  • HTML views(10263)

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