Citation: Lü Jinqiang, Zeng Jing, Abulikemu Abudu Rexit. Highly Active Manganese Dioxide Catalyzed the Construction of S-S Bond[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2483-2490. doi: 10.6023/cjoc201912045 shu

Highly Active Manganese Dioxide Catalyzed the Construction of S-S Bond

Department of Chemistry, Xinjiang Normal University, Urumqi 830054

Corresponding author: Zeng Jing, zengjing800111@163.com Abulikemu Abudu Rexit, aarexit@xjnu.edu.cn
Received Date: 31 December 2019
Revised Date: 12 May 2020
Available Online: 19 May 2020
Fund Project: Project supported by the Scientific Research Program of the Higher Education Institution of Xinjiang (No. XJEDU2020I015), and the Xinjiang Tianshan Youth Program (No. 2017Q026)The Xinjiang Tianshan Youth Program 2017Q026The Scientific Research Program of the Higher Education Institution of Xinjiang XJEDU2020I015

Figures(2)

Generation of highly active manganese dioxide in situ by using catalytic amount of potassium permanganate in anhydrous ethanol system, the catalytic system promoted S-S bond construction by free radical self coupling reactions of thiophenol and mercaptan compounds at room temperature. 14 disulfides were obtained with 70%~99% yields. At the same time, it was also found that the catalytic system could also catalyze radical cross-coupling reactions between symmetric disulfides and different substituents of thiophenols, thiols, or two different symmetric disulfides, 13 asymmetric disulfides were obtained with 19%~72% yields. The protocol offered the advantages of simple and efficient, easy separation, green solvent, wide range of substrate applications, and mild conditions. All products were confirmed by ¹H NMR and ¹³C NMR spectra.
- free radical coupling reaction,
- S-S bond,
- manganese dioxide
1. [1]
  Lin, Y. M.; Yi, W. B. Chin. J. Org. Chem. 2018, 38, 1207(in Chinese).
2. [2]
  Gong, J. X.; Sheng, L.; Yao, L. G.; Li, J.; Zhou, Y. B.; Guo, Y. W. Chin. J. Org. Chem. 2012, 32, 593(in Chinese).
3. [3]
  Su, W. K.; Liang, X. R.; Li, Y. S.; Zhang, Y. M. Chin. J. Org. Chem. 2003, 23, 1019(in Chinese).
4. [4]
  Gong, J, X.; Sun, Y, Q.; Wang, J, D.; Guo, Y, W. Chin. J. Org. Chem. 2008, 28, 252(in Chinese).
5. [5]
  Gong, J. J.; Shen, X.; Yao, L. G.; Jiang, H. L.; Krohn, K.; Guo, Y. W. Org. Lett. 2007, 9, 1715. doi: 10.1021/ol0703783
6. [6]
  Li, X. X.; Lin, S. F.; Chen, J. Nat. Prod. Res. Dev. 2012, 24, 132(in Chinese).
7. [7]
  Halai, R.; Craik, D. J. Nat. Prod. Rep. 2009, 26, 526. doi: 10.1039/b819311h
8. [8]
  Lee, S. H. Arch. Pharm. Res. 2009, 32, 299. doi: 10.1007/s12272-009-1300-4
9. [9]
  Wender, P. A.; Goun, E. A.; Jones, L. R.; Pillow, T. H.; Rothbard, J. B.; Shinde, S.; Contag, C. H. Proc. Nat.l Acad. Sci. U. S. A. 2007, 104, 10340. doi: 10.1073/pnas.0703919104
10. [10]
  Maurela, F.; Debartb, F.; Cavelierc, F.; Thierrya, A. R..; Lebleu, B.; Vasseur, J. J.; Vives, E. Bioorg. Med. Chem. Lett. 2005, 15, 5084. doi: 10.1016/j.bmcl.2005.07.086
11. [11]
  Besret, S.; Ollivier, N.; Blanpain, A.; Melnyk, O. J. Pept. Sci. 2008, 14, 1244. doi: 10.1002/psc.1063
12. [12]
  Gottlieb, D.; Grunwald, C.; Nowak, C.; Kuhlmann, J.; Waldmann, H. Chem. Commun. 2006, 3, 260.
13. [13]
  Alexander, M.; Gerauer, M.; Pechlivanis, M.; Popkirova, B.; Dvorsky, R.; Brunsveld, L.; Waldmann, H.; Kuhlmann, J. ChemBioChem 2009, 10, 98. doi: 10.1002/cbic.200800275
14. [14]
  Dou, Y. C.; Huang, X.; Wang, H.; Yang, L. T.; Li, H.; Yuan, B. X.; Yang, G. Y. Green. Chem. 2017, 19, 2491. doi: 10.1039/C7GC00401J
15. [15]
  Gormer, K.; Waldmann, H.; Triola, G. J. Org. Chem. 2010, 75, 1811. doi: 10.1021/jo902695a
16. [16]
  Huang, P. F.; Wang, P.; Tang, S.; Fu, Z. J.; Lei, A. W. Angew. Chem., Int. Ed. 2018, 57, 8115. doi: 10.1002/anie.201803464
17. [17]
  Stellenboom, N.; Hunter, R.; Caira, M. R. Tetrahedron 2010, 66, 3228. doi: 10.1016/j.tet.2010.02.077
18. [18]
  Yang, F.; Wang, W.; Li, K.; Zhao, W. L.; Dong, X. C. Tetrahedron Lett. 2017, 58, 218. doi: 10.1016/j.tetlet.2016.12.007
19. [19]
  Parida, A.; Choudhuri, K.; Mal, P. Chem. Asian. J. 2019, 14, 2579. doi: 10.1002/asia.201900620
20. [20]
  Noureldin, N. A.; Caldwell, M.; Hendry, J.; Lee, D, G. Synthesis 1998, 1587.
21. [21]
  Shaabani, A.; Tavasoli-Rad, F.; Lee, D. G. Synth. Commun. 2011, 35, 571.
22. [22]
  Liu, S. P.; Qi, Z. J.; Zhang, Z.; Qian, B. Org. Lett. 2019, 21, 7722. doi: 10.1021/acs.orglett.9b02545
23. [23]
  Yang, Y.; Hasimujiang, B.; Rexit, A. A. Chin. J. Org. Chem. 2019, 39, 727(in Chinese).
24. [24]
  Liu, S. Z.; Rexit, A. A. Chemistry Bulletin 2019, 82, 270(in Chinese).
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