Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 6
402
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Metal-Free Highly Efficient Aerobic Oxidation of Sulfides to Sulfoxides Catalyzed by DBDMH/TBN/H2O

, &
Pages 811-819 | Received 14 Mar 2010, Published online: 11 Nov 2011

REFERENCES

  • Hudlicky , M. Oxidations in Organic Chemistry; American Chemical Society : Washington , DC , 1990 .
  • (a) Solladie , G. Comprehensive Organic Synthesis ; B. M. Trost , I. Fleming (Eds.); Pergamon : Oxford , 1991 , vol. 6 , pp. 148 – 170 ; (b) Carreno , M. C. Applications of sulfoxides to asymmetric synthesis of biologically active compounds. Chem. Rev. 1995, 95, 1717–1760 ; (c) Holland , H. L. Chiral sulfoxidation by biotransformation of organic sulfides. Chem. Rev. 1988, 88, 473–485 ; (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 .
  • 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 .
  • (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 ; (b) Bharadwaj , S. K. ; Sharma , S. N. ; Hussain , S. ; Chaudhuri , M. K. Chemoselective sulfoxidation by H2O2 or HNO3 using a phosphate-impregnated titania catalyst . Tetrahedron Lett. 2009 , 50 , 3767 – 3771 .
  • Campestrini , S. ; Tonellato , U. Manganeseporphyrin-catalysed heterogeneous and unusually chemioselective oxidations of sulfides by monopersulfate in supercritical CO2 . J. Mol. Catal. A 2000 , 164 , 263 – 272 .
  • (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; (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; (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; (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.
  • (a) Novitskaya , N. N. ; Chernikova , S. I. Comparative study of the oxidation of sulfides by hydrogen peroxide . Neftekhimiya 1970 , 10 , 429 – 436 ; (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 ; (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 ; (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 ; (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 ; (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 ; (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 ; (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 .
  • (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 ; (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 ; (c) Shii , Y. ; Sakaguchi , S. ; Iwahama , T. Innovation of hydrocarbon oxidation with molecular oxygen and related reactions . Adv. Synth. Catal. 2001 , 343 , 393 – 427 ; (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 ; (e) Ishi , Y. ; Sakaguchi , S. Modern Oxidation Methods; Wiley-VCH: Weinheim, 2004 .
  • Huang , R. L. ; Espenson , J. H. Molecular oxygen reactions catalyzed by an oxorhenium(V) compound . J. Mol. Catal. A: Chem. 2001 , 168 , 39 – 46 .
  • 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 .
  • 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 .
  • 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 .
  • 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 polyoxometalate/hydrogen dinitrate system . J. Mol. Catal. A: Chem. 2006 , 246 , 11 – 17 .
  • 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 .
  • Boring , E. ; Geletii , Y. V. ; Hill , C. L. A homogeneous catalyst for selective O-2 oxidation at ambient temperature: Diversity-based discovery and mechanistic investigation of thioether oxidation by the Au(III)Cl2NO3 (thioether)/O-2 system. J. Am. Chem. Soc. 2001, 123, 1625–1635.
  • (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 ; (b) Komatsu , M. ; Uda , M. ; Suzuki , H. Air oxidation of sulfides to sulfoxides using BiBr3-Bi(NO3)3 as a binary catalyst . Chem. Lett. 1997 , 1229 – 1230 ; (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 ; (d) Firouzabadi , H. ; Iranpoor , N. ; Zolfigol , M. A. Dinitrogen tetroxide 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 ; (f) Martin , S. E. ; Rossi , L. I. An efficient and selective aerobic oxidation of sulfides to sulfoxides catalyzed by Fe(NO3)3-FeBr3 . Tetrahedron Lett. 2001 , 42 , 7147 – 7151 ; (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 .
  • 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 .
  • Wang , X. L. ; Liu , R. H. ; Jin , Y. ; Liang , X. M. TEMPO/HCl/NaNO2 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 .
  • 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 .
  • 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 .
  • 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 .
  • 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 .
  • 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 .
  • Bravo , A. ; Dordi , B. ; Fontana , F. ; Minisci , F. Oxidation of organic sulfides by Br2 and H2O2 electrophilic and free-radical processes . J. Org. Chem. 2001 , 66 , 3232 – 3234 .
  • 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 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.