Metal-free highly efficient aerobic oxidation of sulfides to sulfoxides catalyzed by DBDMH/TBN/H 2O

Synthetic Communications

Volumn 42, Issue 6, 2012, Pages 811-819

  Zhang, Hua ^a   Chen, Chunyu ^a   Liu, Renhua ^b  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

^b EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Aerobic oxidation; DBDMH; Molecular oxygen; Sulfides; Sulfoxides; TBN

Indexed keywords

1 (4 METHANSULFINYLPHENYL)AETHANON; 1,3 DIBROMO 5,5 DIMETHYLHYDANTOIN; 2 CHLOROPHENYLMETHYLSULFOXIDE; 2 METHOXYPHENYLMETHYLSULFOXIDE; 4 CHLOROPHENYLMETHYLSULFOXIDE; 4 FULOROPHENYLMETHYLSULFOXIDE; 4 METHANESULFINYLBENZOIC ACID; 4 METHOXYPHENYLMETHYLSULFOXIDE; 4 METHYLPHENYLMETHYLSULFOXIDE; DIBUTYLSULFOXIDE; HYDANTOIN DERIVATIVE; METHYLPHENYLSULFOXIDE; NITRITE; OXYGEN; SULFIDE; SULFOXIDE; TERT BUTYLNITRITE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED SPECTROSCOPY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE SENSITIVITY;

EID: 84055177677     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.531439     Document Type: Article

References (48)

1. Hudlicky, M. Oxidations in Organic Chemistry; American Chemical Society: Washington, DC, 1990.
2. (a) Solladie, G. Comprehensive Organic Synthesis; B.M. Trost, I. Fleming (Eds.); Pergamon: Oxford, 1991, vol.6, pp.148-170;
3. (b) Carreno, M.C. Applications of sulfox-ides to asymmetric synthesis of biologically active compounds. Chem. Rev. 1995, 95, 1717-1760;
4. (c) Holland, H.L. Chiral sulfoxidation by biotransformation of organic sulfides. Chem. Rev. 1988, 88, 473-485;
5. (d) Block, E. The organosulfur chemistry of the genus Allium-Implications for the organic chemistry of sulfur. Angew Chem., Int. Ed. Engl. 1992, 31, 1135-1178.
6. Xiong, Z.X.; Huang, N.P.; Zhong, P.A selective and convenient oxidation of sulfides to sulfoxides with trichloroisocyanuric acid. Synth. Commun. 2001, 31, 245-248.
7. (a) Compagnini, A.; Santagati, M.; Marziano, N.; Passerini, R. Reaction of nitric acid with aromatic sulfur compounds, VI: Scission of diphenyl sulfides with bromine and nitric acid. Ann. Chim. 1970, 60, 537-542;
8. 3 using a phosphate-impregnated titania catalyst. Tetrahedron Lett. 2009, 50, 3767-3771.
9. 2. J. Mol. Catal. A 2000, 164, 263-272.
10. (a) Ramsden, J.H.; Drago, R.S.; Riley, R.A kinetic study of sulfide oxidation by sodium hypochlorite using phase-transfer catalysis. J. Am. Chem. Soc. 1989, 111, 3958-3961;
11. (b) Zhou, Q.L.; Chen, K.C.; Zhu, Z.H. Asymmetric oxidation of sulfides with FET(α, β, α, β-NAP)PPCL/PHIO/IM system. J. Mol. Catal. 1991, 64, 19-24;
12. (c) Piotr, K.; Katarzyna, M.; Katarzyna, O.; Zofia, K. Oxidation of sulfides to sulfoxides, part 1: Oxidation using halogen derivatives. Tetrahedron 2005, 61, 1933-1953;
13. (d) Huang, J.Y.; Li, S.J.; Wang, Y.G. TEMPO-linked metalloporphyrins as efficient catalysts for selective oxidation of alcohols and sulfides. Tetrahedron Lett. 2006, 47, 5637-5640.
14. (a) Novitskaya, N.N.; Chernikova, S.I. Comparative study of the oxidation of sulfides by hydrogen peroxide. Neftekhimiya 1970, 10, 429-436;
15. (b) Bortolini, O.; Di Furia, F.; Modena, G. Metal catalysis in oxidation by peroxides, 15: Steric effects in the oxidation of organic sulfides with V(V) and MO(VI) peroxocomplexes. J. Mol. Catal. 1982, 16, 61-68;
16. (c) Bortolini, O.; Di Furia, F.; Modena, G. Metal catalysis in oxidation by peroxides, part 16: Kinetics and mechanism of titanium-catalyzed oxidation of sulfides with hydrogen peroxide. J. Mol. Catal. 1982, 16, 69-80;
17. (d) Kaczorowska, K.; Kolarska, Z.; Mitka, K.; Kowalski, P. Oxidation of sulfides to sulfoxides, part 2: Oxidation by hydrogen peroxide. Tetrahedron 2005, 61, 8315-8327;
18. (e) Mba, M.; Prins, L.J.; Licini, G. C3-Symmetric Ti(IV) triphenolate amino complexes as sulfoxidation catalysts with aqueous hydrogen peroxide. Org. Lett. 2007, 9, 21-24;
19. (f) Egami, H.; Katsuki, T. Fe(salan)-catalyzed asymmetric oxidation of sulfides with hydrogen peroxide in water. J. Am. Chem. Soc. 2007, 129, 8940-8941;
20. (g) Shi, X.Y.; Wei, J.F. Selective oxidation of sulfide catalyzed by peroxotungstate, immobilized on ionic liquid-modified silica with aqueous hydrogen peroxide. J. Mol. Catal. A: Chem. 2008, 280, 142-147;
21. (h) Rihara, M.; Yamamoto, J.; Noguchi, T.; Hirai, Y. Selective synthesis of sulfoxides and sulfones by tantalum(V)-catalyzed oxidation of sulfides with 30% hydrogen peroxide. Tetrahedron Lett. 2009, 50, 1180-1183.
22. (a) Mashkina, A.V. Catalytic synthesis of sulfoxides and sulfones via oxidation of sulfides by molecular oxygen. Cat. Rev. Sci. Eng. 1990, 32, 105-161;
23. (b) Iwahama, T.; Sakaguchi, S.; Ishii, Y. Selective oxidation of sulfides to sulfoxides with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) in the presence of alcohols. Tetrahedron Lett. 1998, 39, 9059-9062;
24. (c) Shii, Y.; Sakaguchi, S.; Iwahama, T. Innovation of hydrocarbon oxidation with molecular oxygen and related reactions. Adv. Synth. Catal. 2001, 343, 393-427;
25. (d) Boring, E.; Geletii, Y.V.; Hill, C.L. Catalysis by Metal Complexes; L.I. Simándi (Ed.), Springer: New York, 2003; vol.26, pp.227;
26. (e) Ishi, Y.; Sakaguchi, S. Modern Oxidation Methods; Wiley-VCH: Weinheim, 2004.
27. Huang, R.L.; Espenson, J.H. Molecular oxygen reactions catalyzed by an oxorhe-nium(V) compound. J. Mol. Catal. A: Chem. 2001, 168, 39-46.
28. Aldea, R.; Alper, H. Selective aerobic oxidation of sulfides using a novel palladium complex as the catalyst precursor. J. Org. Chem. 1995, 60, 8365-8366.
29. Zhou, X.T.; Ji, H.B.; Cheng, Z.; Xu, J.C.; Pei, L.X.; Wang, L.F. Selective oxidation of sulfides to sulfoxides catalyzed by ruthenium(III) meso-tetraphenylporphyrin chloride in the presence of molecular oxygen. Bioorg. Med. Chem. Lett. 2007, 17, 4650-4653.
30. Song, G.Q.; Wang, F.; Zhang, H.; Lu, X.L.; Wang, C. Efficient oxidation of sulfides catalyzed by transition metal salts with molecular oxygen in the presence of aldehydes. Synth. Commun. 1998, 28, 2783-2787.
31. Okun, N.M.; Tarr, J.C.; Hilleshiem, D.A.; Zhang, L.; Hardcastle, K.I.; Hill, C.L. Highly reactive catalysts for aerobic thioether oxidation: The Fe-substituted poly-oxometalate/hydrogen dinitrate system. J. Mol. Catal. A: Chem. 2006, 246, 11-17.
32. Dell'Anna, M.M.; Mastrorilli, P.; Nobile, C.F. Aerobic oxidation of sulfides catalysed by cobalt(II) complexes under homogeneous and heterogeneous conditions. J. Mol. Catal. A: Chem. 1996, 108, 57-62.
33. 3 (thioether)/O-2 system. J. Am. Chem. Soc. 2001, 123, 1625-1635.
34. (a) Hirano, M.; Komiya, K.; Yakabe, S.; Clark, J.H.; Morimoto, T.A selective and convenient oxidation of sulfides to sulfoxides with ferric nitrate and silica gel. OPPI Brief. 1996, 28, 705-708;
35. 3 as a binary catalyst. Chem. Lett. 1997, 1229-1230;
36. (c) Kannan, P.; Sevvel, R.; Rajagopal, S.; Pitchumani, K.; Srinivasan, C. Oxidation of organic sulfides with clay-supported iodosylbenzene as oxygen donor. Tetrahedron 1997, 53, 7635-7640;
37. (d) Firouzabadi, H.; Iranpoor, N.; Zolfigol, M.A. Dinitrogen tetrox-ide complexes of Iron(III) and Copper(II) nitrates as new versatile reagents for organic synthesis: Efficient and selective oxidation of sulfides to their corresponding sulfoxides under mild conditions. Synth. Commun. 1998, 28, 377-385;
38. 3. Tetrahedron Lett. 2001, 42, 7147-7151;
39. (g) Kinen, C.O.; Rossi, L.I.; de Rossi, R.H. Chemoselective oxidation of organic sulfides catalyzed by Fe(III) complexes. Appl. Catal. A-Gen. 2006, 312, 120-124.
40. Rossi, L.I.; Suarez, A.R. Transtion metal halides as catalysis in the oxidation reaction of sulfides into sulfoxides. Sulfur Lett. 2002, 5, 123-127.
41. 2 catalyst: A transition-metal-free approach to efficient aerobic oxidation of alcohols to aldehydes and ketones under mild conditions. Chem. Eur. J. 2008, 14, 2679-2685.
42. Bosch, E.; Kochi, J.K. Selective catalysis of thioether oxidations with dioxygen: Critical role of nitrosonium eda complexes in the thermal and photochemical transfer of oxygen atom from nitrogen oxides to sulfur centers. J. Org. Chem. 1995, 60, 3172-3183.
43. Zhang, H.; Chen, C.Y.; Liu, R.H.; Rui, Y. Transition-metal-free approach to highly efficient aerobic oxidation of sulfides to sulfoxides. Synth. Commun. 2008, 38, 4445-4451.
44. Xie, Y.; Mo, W.M.; Xu, D.; Shen, Z.L.; Sun, N.; Hu, B.X.; Hu, X.Q. Efficient NO equivalent for activation of molecular oxygen and its applications in transition-metal-free catalytic aerobic alcohol oxidation. J. Org. Chem. 2007, 72, 4288-4291.
45. Chen, C.Y.; Zhang, H.; Zhang, L.X.; Li, L.D.; Yan, Y.L. HBr/t-BuONO catalysts for activation of oxygen to selective aerobic sulfide oxidation. Chin. J. Org. Chem. 2008, 28, 1978-1981.
46. Liu, R.H.; Dong, C.Y.; Liang, X.M.; Wang, X.J.; Hu, X.Q. Highly efficient catalytic aerobic oxidations of benzylic alcohols in water. J. Org. Chem. 2005, 70, 729-731.
47. 2 electrophilic and free-radical processes. J. Org. Chem. 2001, 66, 3232-3234.
48. Liu, R.H.; Liang, X.M.; Dong, C.Y.; Hu, X.Q. Transition-metal-free: A highly efficient catalytic aerobic alcohol oxidation process. J. Am. Chem. Soc. 2004, 126, 4112-1413.