Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Metalloporphyrin-Catalyzed Chemoselective Oxidation of Sulfides with Polyvinylpyrrolidone-Supported Hydrogen Peroxide: Simple Catalytic System for Selective Oxidation of Sulfides to Sulfoxides

  • Zakavi, Saeed (Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS)) ;
  • Abasi, Azam (School of Chemistry, Damghan University) ;
  • Pourali, Ali Reza (School of Chemistry, Damghan University) ;
  • Talebzadeh, Sadegh (Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS))
  • Received : 2011.08.02
  • Accepted : 2011.10.26
  • Published : 2012.01.20
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Abstract

Room temperature oxidation of organic sulfides with polyvinylpyrrolidone-supported hydrogen peroxide (PVP-$H_2O_2$) in the presence of Mn(III) complexes of meso-tetraphenylporphyrin, Mn(TPP)X (X = OCN, SCN, OAc, Cl) and imidazole (ImH) leads to the highly chemoselective (ca. 90%) oxidation of sulfides to the corresponding sulfoxide. The efficiency of reaction has been shown to be influenced by different reaction parameters such as the nature of counterion (X) and solvent as well as the molar ratio of reactants. Using Mn(TPP)OCN and ImH in 1:15 molar ratio and acetone as the solvent leads to the efficient oxidation of different sulfides.

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References

  1. Backvall, J. E. Selective Oxidation of Amines and Sulfides chapter in Modern Oxidation Methods, Backvall, J. E., Ed.; Wiley-VCH WILEY-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2004.
  2. Fernandez, I.; Khiar N. Chem. Rev. 2003, 103, 3651. https://doi.org/10.1021/cr990372u
  3. Khenkin, A. M.; Neumann, R. J. Am. Chem. Soc. 2002, 124, 4198. https://doi.org/10.1021/ja0178721
  4. Flynn, G. A.; Ash, R. J. Biochem. Biophys. Res. Commun. 1983, 114, 1. https://doi.org/10.1016/0006-291X(83)91585-1
  5. Dai, Y.; Qi, Y.; Zhao, D.; Zhang, H. Fuel Process. Technol. 2008, 89, 927. https://doi.org/10.1016/j.fuproc.2008.03.009
  6. Jones, C. W. Applications of Hydrogen Peroxide and Derivatives; Royal Society of Chemistry: Cambridge, U.K., 1999.
  7. Reddy, T. I.; Varma, R. S. Chem. Commun. 1997, 471.
  8. Iranpoor, N.; Mohajer, D.; Rezaeifard, A. Tetrahedron. Lett. 2004, 45, 3811. https://doi.org/10.1016/j.tetlet.2004.03.082
  9. Ghaemi, A.; Rayati, S.; Zakavi, S.; Safari, N. Appl. Catal. A 2009, 353, 154. https://doi.org/10.1016/j.apcata.2008.10.043
  10. Zhou, X.-T.; Ji, H.-B.; Cheng, Z.; Xu, J.-C.; Pei, L.-X.; Wang, L. F. Bioorg. Med. Chem. Lett. 2007, 17, 4650. https://doi.org/10.1016/j.bmcl.2007.05.073
  11. Huang, J.-Y.; Li, S.-J.; Wang, Y.-G. Tetrahedron. Lett. 2006, 47, 5637. https://doi.org/10.1016/j.tetlet.2006.06.039
  12. Pourali, A. R.; Ghanei, M. Chin. J. Chem. 2006, 24, 1077. https://doi.org/10.1002/cjoc.200690201
  13. Pourali, A. R.; Ghanei, M. Bull. Korean Chem. Soc. 2006, 27, 1674. https://doi.org/10.5012/bkcs.2006.27.10.1674
  14. Zakavi, S.; Abasi, A.; Pourali, A. R.; Rayati, S. Bull. Korean Chem. Soc. 2008, 29, 866. https://doi.org/10.5012/bkcs.2008.29.4.866
  15. Mohajer, D.; Karimipour, G.; Bagherzadeh, M. New J. Chem. 2004, 28, 740. https://doi.org/10.1039/b310909g
  16. Mohajer, D.; Tayebee, R.; Goudarziafshar, H. J. Chem. Res. S 1999, 168.
  17. Nam, W. Acc. Chem. Res. 2007, 40, 522. https://doi.org/10.1021/ar700027f
  18. Rayati, S.; Zakavi, S.; Noroozi, V. J. Sulfur. Chem. 2010, 31, 89. https://doi.org/10.1080/17415990903569551
  19. Nam, W.; Lim, M. H.; Lee, H. J.; Kim, C. J. Am. Chem. Soc. 2000, 122, 6641. https://doi.org/10.1021/ja000289k
  20. Jeffery, G. H.; Bassett, J.; Mendham, J.; Denney, R. D. Vogel's Textbook of Quantitative Chemical Analysis, 5th ed.; John Wiley & Sons: New York, 1989.
  21. Adler, A. D.; Longo, F. R.; Kampas, F.; Kim, J. J. Inorg. Nucl. Chem. 1970, 32, 2443. https://doi.org/10.1016/0022-1902(70)80535-8
  22. Adler, A. D. J. Org. Chem. 1967, 32, 476.
  23. Mohajer, D.; Abbasi, M. Eur. J. Inorg. Chem. 2008, 3218.
  24. Ogoshi, H.; Watanabe, E.; Yoshida, Z.; Kincaid, J.; Nakamoto, K. J. Am. Chem. Soc. 1973, 95, 2845. https://doi.org/10.1021/ja00790a017
  25. Mohajer, D.; Sadeghian, L. J. Mol. Catal. A: Chem. 2007, 272, 191. https://doi.org/10.1016/j.molcata.2007.03.033
  26. Mansuy, D.; Battioni, P. in The Porphyrin Handbook; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, U.S., 2000.
  27. Nam, W.; Lim, M. H.; Oh, S.-Y. Inorg. Chem. 2000, 39, 5572. https://doi.org/10.1021/ic000502d
  28. Nam, W.; Jin, S. W.; Lim, M. H.; Ryu, J. Y.; Kim, C. Inorg. Chem. 2002, 41, 3647. https://doi.org/10.1021/ic011145p
  29. Andini, S.; Castronuovo, G.; Elia, V.; Pignone, A.; Velleca, F. J. Solution Chem. 1996, 25, 825. https://doi.org/10.1007/BF00972575
  30. Ali, M. H.; Bohnert, G. J. Synthesis 1998, 1238.
  31. Zhang, R.; Horner, J. H. Newcomb, M. J. Am. Chem. Soc. 2005, 127, 6573. https://doi.org/10.1021/ja045042s

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