Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Chemoselective Oxidation of Sulfides Promoted by a Tightly Convoluted Polypyridinium Phosphotungstate Catalyst with H2O2

  • Jin, Chung Keun (RIKEN Advanced Science Institute) ;
  • Yamada, Yoichi M. A. (Institute for Molecular Science (IMS)) ;
  • Uozumi, Yasuhiro (RIKEN Advanced Science Institute)
  • Published : 2010.03.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Clayden, C.; Greeves, N.; Warren, S.; Wothers, P. Organo main group Chemistry 1: Sulfur in Organic Chemistry (Ch. 47); Oxford: New York, 2001.
  2. Patai, S.; Rappoport, H.; Sterling, J. J. The Chemistry of Sulfones and Sulfoxide; Wiley: New York, 1988.
  3. Oae, S. In The Organic Chemistry of Sulfur; Plenum: New York, 1977.
  4. Franzel, T.; Solodenko, W.; Kirschning, A. Solid‐Phase Bound Catalysts: Properties and Applications in Polymeric Materials in Organic Synthesis and Catalysis (Ch. 4); Buchmeiser, M. R., Ed., Wiley-VCH: Weinheim, 2003.
  5. Wang, Z. ; Chen, G.; Ding, K. Chem. Rev. 2009, 109, 322. https://doi.org/10.1021/cr800406u
  6. Lu, J.; Toy, P. H. Chem. Rev. 2009, 109, 815. https://doi.org/10.1021/cr8004444
  7. Dell’Anna, M. M.; Mastrorilli, P.; Nobile, C. F. J. Mol. Catal. A: Chem. 1996, 108, 57-62. https://doi.org/10.1016/1381-1169(95)00302-9
  8. Alcon, M. J.; Corma, A.; Iglesias, M.; Sanchez, F. J. Mol. Catal. A: Chem. 2002, 178, 253-266. https://doi.org/10.1016/S1381-1169(01)00336-3
  9. Koo, D. H.; Kim, M.; Chang, S. Org. Lett. 2005, 7, 5015. https://doi.org/10.1021/ol052019i
  10. Kasai, J.; Nakagawa, Y.; Uchida, S.; Yamaguchi, K.; Mizuno, N. Chem. Eur. J. 2006, 12, 4176. https://doi.org/10.1002/chem.200501414
  11. Shaabani, A.; Rezayan, A. H. Catal. Commun. 2007, 8, 1112. https://doi.org/10.1016/j.catcom.2006.10.033
  12. Venkat Reddy, C.; Verkade, J. G. J. Mol. Catal. A: Chem. 2007, 272, 233. https://doi.org/10.1016/j.molcata.2007.02.053
  13. Kirihara, M.; Yamamoto, J.; Noguchi, T.; Hirai, Y. Tetrahedron Lett. 2009, 50, 1180. https://doi.org/10.1016/j.tetlet.2008.12.064
  14. Bharadwaj, S. K.; Sharma, S. N.; Hussain, S.; Chaudhuri, M. K. Tetrahedron Lett. 2009, 50, 3767. https://doi.org/10.1016/j.tetlet.2009.03.106
  15. Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140-1142. https://doi.org/10.1021/jo01039a512
  16. Stec, Z.; Zawadiak, J.; Skibinski, A.; Pastuch, G. Polish J. Chem. 1996, 70, 1121-1123.
  17. Neumann, R.; Juwiler, D. Tetrahedron 1996, 52, 8781-8788. https://doi.org/10.1016/0040-4020(96)00419-X
  18. Gresley, N. M.; Griffith, W. P.; Laemmel, A. C.; Nogueira, H. I. S.; Perkin, B. C. J. Mol. Catal. 1997, 117, 185-198. https://doi.org/10.1016/S1381-1169(96)00256-7
  19. Collins, F. M.; Lucy, A. R.; Sharp, C. J. Mol. Catal. 1997, 117, 397-403. https://doi.org/10.1016/S1381-1169(96)00251-8
  20. Yasuhara, Y.; Yamaguchi, S.; Ichihara, J.; Nomoto, T.; Sasaki, Y. Phosphorus Res. Bull. 2000, 11, 43-46. https://doi.org/10.3363/prb1992.11.0_43
  21. Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X.-Q.; Noyori, R. Tetrahedron 2001, 57, 2469-2476. https://doi.org/10.1016/S0040-4020(01)00068-0
  22. Shi, X.-Y.; Wei, J.-F. J. Mol. Catal. A: Chem. 2008, 280, 142. https://doi.org/10.1016/j.molcata.2007.11.002
  23. Yamada, Y. M. A. Chem. Pharm. Bull. 2005, 53, 723 (review). https://doi.org/10.1248/cpb.53.723
  24. Yamada, Y. M. A.; Uozumi,Y. Tetrahedron 2007, 63, 8492. https://doi.org/10.1016/j.tet.2007.05.071
  25. Yamada,Y. M. A.; Maeda, Y.; Uozumi, Y. Org. Lett. 2006, 8, 4259. https://doi.org/10.1021/ol0615026
  26. Yamada, Y. M. A.; Uozumi, Y. Org. Lett. 2006, 8, 1375. https://doi.org/10.1021/ol060166q
  27. Yamada, Y. M. A.; Tabata, H.; Takahashi, H.; Ikegami, S. Synlett 2002, 2031.
  28. Yamada, Y. M. A.; Tabata, H.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Tetrahedron 2004, 60, 4097. https://doi.org/10.1016/j.tet.2004.02.068
  29. Yamada, Y. M. A.; Ichinohe, M.; Takahashi, H.; Ikegami, S. Org. Lett. 2001, 3, 1837. https://doi.org/10.1021/ol015863r
  30. Hamamoto, H.; Suzuki, H.; Yamada, Y. M. A.; Tabata, H.; Takahashi, H.; Ikegami, S. Angew. Chem. Int. Ed. 2005, 44, 4536. https://doi.org/10.1002/anie.200500574
  31. Yamada, Y. M. A.; Guo, H.; Uozumi, Y. Org. Lett. 2007, 9, 1501. https://doi.org/10.1021/ol070258v
  32. Yamada, Y. M. A.; Guo, H.; Uozumi, Y. Heterocycles 2008, 76, 645. https://doi.org/10.3987/COM-08-S(N)56

Cited by

  1. Development of Polymeric Metal Catalysts via Molecular Convolution and of Catalytic Membrane-Installed Microflow Devices vol.69, pp.5, 2011, https://doi.org/10.5059/yukigoseikyokaishi.69.542
  2. Catalyst-free oxidation of sulfides to sulfoxides and diethylamine catalyzed oxidation of sulfides to sulfones using Oxone as an oxidant vol.43, pp.12, 2017, https://doi.org/10.1007/s11164-017-3026-0
  3. ChemInform Abstract: Chemoselective Oxidation of Sulfides Promoted by a Tightly Convoluted Polypyridinium Phosphotungstate Catalyst with H2O2. vol.41, pp.31, 2010, https://doi.org/10.1002/chin.201031041
  4. Selected methods for the synthesis of sulfoxides and sulfones with emphasis on oxidative protocols vol.195, pp.3, 2010, https://doi.org/10.1080/10426507.2019.1672691