Sulfamic acid-catalyzed oxidation of sulfides to sulfoxides and sulfones using H 2O 2: Green and chemoselective method

Synthetic Communications

Volumn 42, Issue 21, 2012, Pages 3150-3156

  Jafari, Hadi ^a   Rostami, Amin ^b   Ahmad Jangi, Firoz ^b   Ghorbani Choghamarani, Arash ^c  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b UNIVERSITY OF KURDISTAN   (Iran)

^c ILAM UNIVERSITY   (Iran)

Author keywords

Catalyst; hydrogen peroxide; oxidation; sulfamic acid; sulfide; sulfone; sulfoxide

Indexed keywords

ALCOHOL; ALDEHYDE; ESTER; HYDROGEN PEROXIDE; SULFAMIC ACID; SULFIDE; SULFONE; SULFOXIDE; SULFUR ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; GREEN CHEMISTRY; ROOM TEMPERATURE; SULFOXIDATION; SYNTHESIS;

EID: 84865519148     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.577924     Document Type: Article

References (30)

1. Fernandez, I.; Khiar, N. Recent developments in the synthesis and utilization of chiral sulfoxides. Chem. Rev. 2003, 103, 3651-3706.
2. Campos-Martin, J.; Capel-Sanchez, M.; Fierro, J. Highly efficient deep desulfurization of fuels by chemical oxidation. Green Chem. 2004, 6, 557-562.
3. Orito, K.; Hatakeyama, T.; Takeo, M.; Suginome, H. Oxidation with mercury(II) oxide-iodine reagent: Selective oxidation of sulfides to sulfoxides. Synthesis 1995, 1357-1358.
4. Batigalhia, F.; Zaldini-Hernandes, M.; Ferreira, A. G.; Malvestiti, I.; Cass, Q. B. Selective and mild oxidation of sulfides to sulfoxides by oxodiperoxo molybdenum complexes adsorbed onto silica gel. Tetrahedron 2001, 57, 9669-9676. (Pubitemid 33044720)
5. Xu, L.; Cheng, J.; Trudell, M. L. Chromium(VI) oxide-catalyzed oxidation of sulfides to sulfones with periodic acid. J. Org. Chem. 2003, 68, 5388-5391. (Pubitemid 36750218)
6. Habibi, D.; Zolfigol, M. A.; Safaiee, M.; Shamsian, A.; Ghorbani-Choghamarani, A. Catalytic oxidation of sulfides to sulfoxides using sodium perborate and=or sodium percarbonate and silica sulfuric acid in the presence of KBr. Catal. Commun. 2009, 10, 1257-1260.
7. Gomez, M. V.; Caballero, R.; Vazquez, E.; Moreno, A.; Hoz, A. D. L.; Diaz-Ortiz, A. Green and chemoselective oxidation of sulfides with sodium perborate and sodium percarbonate: Nucleophilic and electrophilic character of the oxidation system. Green Chem. 2007, 9, 331-336.
8. Page, P. C. B.; Graham, A. E.; Bethell, D.; Park, B. K. A simple and convenient method for the oxidation of sulfides. Synth. Commun. 1993, 23, 1507-1514. (Pubitemid 23190950)
9. Bethell, D.; Graham, A. E.; Heer, J. P.; Markopoulou, O.; Page, P. C. B.; Park, B. K. Reactivity and selectivity in the oxidation of aryl methyl sulfides and sulfoxides by hydrogen peroxide mediated by acetonitrile. J. Chem. Soc., Perkin Trans. 2 1993, 2, 2161-2162.
10. Page, P. C. B.; Bethell, D.; Stocks, P. A.; Heer, J. P.; Graham, A. E.; Vahedi, H.; Healy, M.; Collington, E. W.; Andrews, D. M. Sulfur oxidation mediated by imine derivatives. Synlett 1997, 1355-1358. (Pubitemid 127719929)
11. Bethell, D.; Page, P. C. B.; Vahedi, H. Catalytic asymmetric oxidation of sulfides to sulfoxides mediated by chiral 3-substituted-1,2-benzisothiazole 1,1-dioxides. J. Org. Chem. 2000, 65, 6756-6760.
12. Robinson, D. J.; Davies, L.; McGuire, N.; Lee, D. F.; McMorn, P.; Willock, D. J.; Watson, G. W.; Page, P. C. B.; Bethell, D.; Hutchings, G. J. Oxidation of thioethers and sulfoxides with hydrogen peroxide using TS-1 as catalyst. Phys. Chem. Chem. Phys. 2000, 2, 1523-1529.
13. Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X. Q.; Noyori, R. Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent and halogen-free conditions. Tetrahedron 2001, 57, 2469-2476. (Pubitemid 32239497)
14. Choudary, B. M.; Bharathi, B.; Reddy, C. V.; Kantam, M. L. Tungstate-exchanged Mg-Al-LDH catalyst: An eco-compatible route for the oxidation of sulfides in aqueous medium. J. Chem. Soc., Perkin. Trans. 1 2002, 2069-2074.
15. Jeyakumar,K.; Chand, D. K. Selective oxidation of sulfides to sulfoxides and sulfones at room temperature using H2O2 and aMo(VI) salt as catalyst. Tetrahedron Lett. 2006, 47, 4573-4576. (Pubitemid 43815500)
16. Romanelli, G. P.; Bennardi, D. O.; Palermo, V.; Vazquez, P. G.; Tundo, P. Vanadium-substituted Keggin-type heteropolyacid are used for the selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide. Lett. Org. Chem. 2007, 4, 544-549.
17. Shaabani, A.; Rezayan, A. H. Silica sulfuric acid-promoted selective oxidation of sulfides to sulfoxides or sulfones in the presence of aqueous H2O2. Catal. Commun. 2007, 8, 1112-1116. (Pubitemid 46720116)
18. Zali, A.; Shokrolahi, A.; Keshavarz, M. H.; Zarei, M. A. Carbon-based solid acid-catalyzed highly efficient selective oxidations of sulfides to sulfoxides or sulfones with hydrogen peroxide. Acta. Chim. Slov. 2008, 55, 257-260.
19. (V) Kirihara, M.; Yamamoto, J.; Noguchi, T.; Hirai, Y. Selective synthesis of sulfoxides and sulfones by tantalum-catalyzed oxidation of sulfides with 30% hydrogen peroxide. Tetrahedron Lett. 2009, 50, 1180-1183.
20. (V) Kirihara, M.; Itou, A.; Noguchi, T.; Yamamoto, J. Tantalum carbide-or niobium carbide-catalyzed oxidation of sulfides with hydrogen peroxide: Highly efficient and chemoselective syntheses of sulfoxides and sulfones. Synlett 2010, 1557-1561.
21. Rahimizadeh, M.; Rajabzadeh, G.; Khatami, S.-M.; Eshghi, H.; Shiri, A. TiO2 nanoparticles and Preyssler-type heteropoly acid modified nano-sized TiO2: A facile and efficient catalyst for the selective oxidation of sulfides to sulfones and sulfoxides. J. Mol. Catal. A: Chem. 2010, 323, 59-64.
22. Bahrami, K.; Khodaei, M. M.; Sheikh-Arabi, M. TAPC-promoted oxidation of sulfides and deoxygenation of sulfoxides. J. Org. Chem. 2010, 75, 6208-6213.
23. Romanelli, G. P.; Villabrille, P. I.; Cáceresa, C. V.; Vázquez, P. G.; Tundo, P. Keggin heteropolycompounds as catalysts for liquid-phase oxidation of sulfides to sulfoxides= sulfones by hydrogen peroxide. Catal. Commun. 2011, 12, 726-730.
24. Maayan, G.; Popovitz-Biro, R.; Neumann, R. Micelle directed synthesis of polyoxometalate nanoparticles and their improved catalytic activity for the aerobic oxidation of sulfides. J. Am. Chem. Soc. 2006, 128, 4968-4969.
25. Heravi, M. M.; Baghernejad, B.; Oskooie, H. A. Application of sulfamic acid in organic synthesis-A short review. Curr. Org. Chem. 2009, 13, 1002-1014.
26. Heravi, M. M.; Derikvand, F.; Ranjbar, L. Sulfamic acid-catalyzed, three-component, one-pot synthesis of [1,2,4]triazolo=benzimidazolo quinazolinone derivatives. Synth. Commun. 2010, 40, 677-685.
27. Rostami, A.; Rahmati, S.; Khazaei, A. A highly efficient and eco-friendly procedure for tetrahydropyranylation of alcohols and phenols in the presence of insitu generated I2 under heterogeneous and neutral conditions. Monatsh. Chem. 2009, 140, 663-667.
28. Rostami, A.; Akradi, J. A highly efficient, green, rapid, and chemoselective oxidation of sulfides using hydrogen peroxide and boric acid as the catalyst under solvent-free conditions. Tetrahedron Lett. 2010, 51, 3501-3503.
29. Rostami, A.; Ahmad-Jangi, F.; Zarehbin, M. R.; Akradi, J. Green and efficient procedure for the trimethylsilylation of hydroxy groups and their regeneration using sulfamic acid as recyclable catalyst. Synth. Commun. 2010, 40, 1500-1507.
30. Pouchert, C. J.; Behnke, J. The Aldrich Library of 13C and 1H FT NMR Spectra; 1st ed.; Aldrich Chemical Company: Milwaukee, WI, 1993; vol. 1.