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Volumn 49, Issue 5, 2010, Pages 2533-2536

A simple and environmentally benign method for sulfoxidation of sulfides with hydrogen peroxide

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL SULFIDES; ENVIRONMENTALLY BENIGN; INDUSTRIAL PRODUCTION; MEDIATED REACTIONS; SULFOXIDATION;

EID: 77749304431     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie9017572     Document Type: Article
Times cited : (28)

References (41)
  • 4
    • 14644413473 scopus 로고    scopus 로고
    • Applications of catalytic asymmetric sulfide oxidations to the syntheses of biologically active sulfoxides
    • Legros, J.; Dehli, J. R.; Bolm, C. Applications of Catalytic Asymmetric Sulfide Oxidations to the Syntheses of Biologically Active Sulfoxides. Adv. Synth. Catal. 2005, 347, 19.
    • (2005) Adv. Synth. Catal. , vol.347 , pp. 19
    • Legros, J.1    Dehli, J.R.2    Bolm, C.3
  • 5
    • 11944251609 scopus 로고
    • Applications of sulfoxides to asymmetric synthesis of biologically active compounds
    • Carreno, M. C. Applications of Sulfoxides to Asymmetric Synthesis of Biologically Active Compounds. Chem. Rev. 1995, 95, 1717.
    • (1995) Chem. Rev. , vol.95 , pp. 1717
    • Carreno, M.C.1
  • 6
    • 0141508049 scopus 로고    scopus 로고
    • Recent developments in the synthesis and utilization of chiral sulfoxides
    • Fernández, N.; Khiar, I. Recent Developments in the Synthesis and Utilization of Chiral Sulfoxides. Chem. Rev. 2003, 103, 3651.
    • (2003) Chem. Rev. , vol.103 , pp. 3651
    • Fernández, N.1    Khiar, I.2
  • 7
    • 0037765617 scopus 로고    scopus 로고
    • Benzyltriphenylphosphonium chlorochromate (BTPPCC): An efficient and novel reagent for oxidation of sulfides to the corresponding sulfoxides under non-aqueous conditions
    • Hajipour, A. R.; Ruoho, A. E. Benzyltriphenylphosphonium Chlorochromate (BTPPCC): An Efficient and Novel Reagent for Oxidation of Sulfides to the Corresponding Sulfoxides under Non-aqueous Conditions. Sulfur Lett. 2003, 26, 83.
    • (2003) Sulfur Lett. , vol.26 , pp. 83
    • Hajipour, A.R.1    Ruoho, A.E.2
  • 8
    • 54049139509 scopus 로고    scopus 로고
    • Catalytic oxidation of sulfides to sulfoxide using manganese(III) complexes with bidentate O,N-donor oxazoline ligand and UHP oxidizing agent
    • Bagherzadeh, M.; Latifi, R.; Tahsini, L.; Amini, M. Catalytic Oxidation of Sulfides to Sulfoxide Using Manganese(III) Complexes with Bidentate O,N-donor Oxazoline Ligand and UHP Oxidizing Agent. Catal. Commun. 2008, 10, 196.
    • (2008) Catal. Commun. , vol.10 , pp. 196
    • Bagherzadeh, M.1    Latifi, R.2    Tahsini, L.3    Amini, M.4
  • 9
    • 0035804984 scopus 로고    scopus 로고
    • Oxidation of organic sulfides by Br and HO electrophilic and free-radical processes
    • Bravo, A.; Dordi, B.; Fontana, F.; Minisci, F. Oxidation of Organic Sulfides by Br and HO Electrophilic and Free-Radical Processes. J. Org. Chem. 2001, 66, 3232.
    • (2001) J. Org. Chem. , vol.66 , pp. 3232
    • Bravo, A.1    Dordi, B.2    Fontana, F.3    Minisci, F.4
  • 10
    • 14844353084 scopus 로고    scopus 로고
    • Selective oxidation of sulfides to sulfoxides using 30% hydrogen peroxide catalyzed with a recoverable silica-based tungstate interphase catalyst
    • Karimi, B.; Nezhad, M. G.; Clark, J. H. Selective Oxidation of Sulfides to Sulfoxides Using 30% Hydrogen Peroxide Catalyzed with a Recoverable Silica-Based Tungstate Interphase Catalyst. Org. Lett. 2005, 7, 625.
    • (2005) Org. Lett. , vol.7 , pp. 625
    • Karimi, B.1    Nezhad, M.G.2    Clark, J.H.3
  • 11
    • 0037195744 scopus 로고    scopus 로고
    • Selective and efficient oxidation of sulfides and thiols with benzyltriphenylphosphonium peroxymonosulfate in aprotic solvent
    • Hajipour, A. R.; Mallakpour, S. E.; Adibi, H. Selective and Efficient Oxidation of Sulfides and Thiols with Benzyltriphenylphosphonium Peroxymonosulfate in Aprotic Solvent. J. Org. Chem. 2002, 67, 8666.
    • (2002) J. Org. Chem. , vol.67 , pp. 8666
    • Hajipour, A.R.1    Mallakpour, S.E.2    Adibi, H.3
  • 12
    • 0029849815 scopus 로고    scopus 로고
    • Simple and efficient method for the oxidation of sulfides to sulfoxides: Application to the preparation of glycosyl sulfoxides
    • Kakarla, R.; Dulina, R. G.; Hatzenbuhler, N. T.; Hui, Y. W.; Sofia, M. J. Simple and Efficient Method for the Oxidation of Sulfides to Sulfoxides: Application to the Preparation of Glycosyl Sulfoxides. J. Org. Chem. 1996, 61, 8347.
    • (1996) J. Org. Chem. , vol.61 , pp. 8347
    • Kakarla, R.1    Dulina, R.G.2    Hatzenbuhler, N.T.3    Hui, Y.W.4    Sofia, M.J.5
  • 13
    • 0034630941 scopus 로고    scopus 로고
    • Surface-mediated reactions. 8. Oxidation of sulfides and sulfoxides with tert-butyl hydroperoxide and OXONE
    • Kropp, P. J.; Breton, G. W.; Fields, J. D.; Tung, J. C.; Loomis, B. R. Surface-Mediated Reactions. 8. Oxidation of Sulfides and Sulfoxides with tert-Butyl Hydroperoxide and OXONE. J. Am. Chem. Soc. 2000, 122, 4280.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4280
    • Kropp, P.J.1    Breton, G.W.2    Fields, J.D.3    Tung, J.C.4    Loomis, B.R.5
  • 14
    • 5444241573 scopus 로고    scopus 로고
    • A simple and selective oxidation of sulfides to sulfoxides using tetrabutylammonium Peroxydisulfate: A rebuttal
    • Park, M. Y.; Jadhav, V.; Kim, Y. H. A Simple and Selective Oxidation of Sulfides to Sulfoxides Using Tetrabutylammonium Peroxydisulfate: A Rebuttal. Synth. Commun. 2004, 34, 3367.
    • (2004) Synth. Commun. , vol.34 , pp. 3367
    • Park, M.Y.1    Jadhav, V.2    Kim, Y.H.3
  • 16
    • 0000057992 scopus 로고
    • Peroxytrifluoroacetic acid. A convenient reagent for the preparation of sulfoxides and sulfones
    • Venier, C. G.; Squires, T. G.; Chen, Y. Y.; Hussmann, G. P.; Shei, J. C.; Smith, B. F. Peroxytrifluoroacetic acid. A convenient Reagent for the Preparation of Sulfoxides and Sulfones. J. Org. Chem. 1982, 47, 3773.
    • (1982) J. Org. Chem. , vol.47 , pp. 3773
    • Venier, C.G.1    Squires, T.G.2    Chen, Y.Y.3    Hussmann, G.P.4    Shei, J.C.5    Smith, B.F.6
  • 17
    • 3542997595 scopus 로고
    • A biphasic process for the oxidation of sulfides: A new convenient route to sulfoxides
    • Gasparrini, F.; Giovannoli, M.; Maresca, L.; Natile, G.; Palmieri, G. A Biphasic Process for the Oxidation of Sulfides: A New Convenient Route to Sulfoxides. Synth. Commun. 1984, 14, 1111.
    • (1984) Synth. Commun. , vol.14 , pp. 1111
    • Gasparrini, F.1    Giovannoli, M.2    Maresca, L.3    Natile, G.4    Palmieri, G.5
  • 18
    • 28844463985 scopus 로고    scopus 로고
    • 2: A mild and efficient reagent for selective oxidation of sulfides to sulfoxides under solvent-free condition
    • 2: A Mild and Efficient Reagent for Selective Oxidation of Sulfides to Sulfoxides under Solvent-free Condition. Synth. Commun. 2005, 36, 807.
    • (2005) Synth. Commun. , vol.36 , pp. 807
    • Lakouraj, M.M.1    Tajbakhsh, M.2    Shirini, F.3    Asady Tamani, M.V.4
  • 19
    • 33845554571 scopus 로고
    • Mechanism of the oxidation of Alkyl Aryl sulfides by phenyliodoso diacetate
    • Srinivasan, C.; Chellamani, A.; Kuthalingam, P. Mechanism of the Oxidation of Alkyl Aryl Sulfides by Phenyliodoso Diacetate. J. Org. Chem. 1982, 47, 428.
    • (1982) J. Org. Chem. , vol.47 , pp. 428
    • Srinivasan, C.1    Chellamani, A.2    Kuthalingam, P.3
  • 20
    • 0032543458 scopus 로고    scopus 로고
    • Hypervalent iodine(III) oxidation catalyzed by quaternary ammonium salt in micellar systems
    • Tohama, H.; Takizawa, S.; Watanabe, H.; Kita, Y. Hypervalent iodine(III) Oxidation Catalyzed by Quaternary Ammonium Salt in Micellar Systems. Tetrahedron Lett. 1998, 39, 4547.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 4547
    • Tohama, H.1    Takizawa, S.2    Watanabe, H.3    Kita, Y.4
  • 21
    • 0030981424 scopus 로고    scopus 로고
    • Hypervalent Iodine in synthesis XXIII: Oxidation with [hydroxyl(tosyloxy)iodo]benzene: Selective oxidation of sulfides to sulfoxides
    • Xia, M.; Chen, Z. C. Hypervalent Iodine in Synthesis XXIII: Oxidation with [hydroxyl(tosyloxy)iodo]benzene: Selective Oxidation of Sulfides to Sulfoxides. Synth. Commun. 1997, 27, 1315.
    • (1997) Synth. Commun. , vol.27 , pp. 1315
    • Xia, M.1    Chen, Z.C.2
  • 22
    • 0037532988 scopus 로고    scopus 로고
    • A mild chemoselective oxidation of sulfides to sulfoxides using o-iodoxybenzoic acid and tetraethylammonium bromide as catalyst
    • Shukla, V. G.; Salgaonkar, P. D.; Akamanchi, K. G. A Mild, Chemoselective Oxidation of Sulfides to Sulfoxides Using o-Iodoxybenzoic Acid and Tetraethylammonium Bromide as Catalyst. J. Org. Chem. 2003, 68, 5422.
    • (2003) J. Org. Chem. , vol.68 , pp. 5422
    • Shukla, V.G.1    Salgaonkar, P.D.2    Akamanchi, K.G.3
  • 24
    • 38049188185 scopus 로고    scopus 로고
    • Vanadium-substituted keggin type heteropolyacid are used for the selective oxidation of sulfides to sulfoxides and sulfones using hydrogen peroxide
    • Romanelli, G. P.; Bennardi, D. O.; Palermo, V.; Vázquez, 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.
    • (2007) Lett. Org. Chem. , vol.4 , pp. 544
    • Romanelli, G.P.1    Bennardi, D.O.2    Palermo, V.3    Vázquez, P.G.4    Tundo, P.5
  • 25
    • 29144431522 scopus 로고    scopus 로고
    • Catalytic oxidation of a thioether and dibenzothiophenes using an oxorhenium(V) dithiolate complex tethered on silica
    • Stanger, K. J.; Wiench, J. W.; Pruski, M.; Espenson, J. H.; Kraus, G. A.; Angelici, R. J. Catalytic Oxidation of a Thioether and Dibenzothiophenes Using an Oxorhenium(V) Dithiolate Complex Tethered on Silica. J. Mol. Catal. A 2006, 243, 158.
    • (2006) J. Mol. Catal. A , vol.243 , pp. 158
    • Stanger, K.J.1    Wiench, J.W.2    Pruski, M.3    Espenson, J.H.4    Kraus, G.A.5    Angelici, R.J.6
  • 26
    • 57849123634 scopus 로고    scopus 로고
    • Characterization and catalytic study of a novel iron(III)-tridentate schiff base complex in sulfide oxidation by UHP
    • Bagherzadeh, M.; Amini, M. Synthesis, Characterization and Catalytic Study of a Novel Iron(III)-tridentate Schiff Base Complex in Sulfide Oxidation by UHP. Inorg. Chem. Commun. 2009, 12, 21.
    • (2009) Inorg. Chem. Commun. , vol.12 , pp. 21
    • Bagherzadeh, M.1    Synthesis, A.M.2
  • 27
    • 2442502432 scopus 로고    scopus 로고
    • Synthesis of sulfoxides by the hydrogen peroxide induced oxidation of sulfides catalyzed by iron tetrakis(pentafluorophenyl)porphyrin: Scope and chemoselectivity
    • Baciocchi, E.; Gerini, M. F.; Lapi, A. Synthesis of Sulfoxides by the Hydrogen Peroxide Induced Oxidation of Sulfides Catalyzed by Iron Tetrakis(pentafluorophenyl)porphyrin: Scope and Chemoselectivity. J. Org. Chem. 2004, 69, 3586.
    • (2004) J. Org. Chem. , vol.69 , pp. 3586
    • Baciocchi, E.1    Gerini, M.F.2    Lapi, A.3
  • 28
    • 34547406870 scopus 로고    scopus 로고
    • (Salan)-catalyzed asymmetric oxidation of sulfides with hydrogen peroxide in water
    • Egami, H.; Katsuk, T. Fe (salan)-Catalyzed Asymmetric Oxidation of Sulfides with Hydrogen Peroxide in Water. J. Am. Chem. Soc. 2007, 129, 8941.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 8941
    • Egami, H.1    Fe, K.T.2
  • 30
    • 0344845085 scopus 로고    scopus 로고
    • Iron-catalyzed asymmetric sulfide oxidation with aqueous hydrogen peroxide
    • Legros, J.; Bolm, C. Iron-Catalyzed Asymmetric Sulfide Oxidation with Aqueous Hydrogen Peroxide. Angew. Chem., Int. Ed. 2003, 42, 5487.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5487
    • Legros, J.1    Bolm, C.2
  • 31
    • 4644283019 scopus 로고    scopus 로고
    • Highly enantioselective iron-catalyzed sulfide oxidation with aqueous hydrogen peroxide under simple reaction conditions
    • Legros, J.; Bolm, C. Highly Enantioselective Iron-Catalyzed Sulfide Oxidation with Aqueous Hydrogen Peroxide under Simple Reaction Conditions. Angew. Chem., Int. Ed. 2004, 43, 4225.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 4225
    • Legros, J.1    Bolm, C.2
  • 32
    • 27744568390 scopus 로고    scopus 로고
    • Sulfide oxygenation by tert-butyl hydroperoxide with mononuclear (Me3TACN) Mn catalysts
    • Barker, J. E.; Ren, T. Sulfide Oxygenation by Tert-butyl Hydroperoxide with Mononuclear (Me3TACN) Mn Catalysts. Tetrahedron Lett. 2005, 46, 6805.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 6805
    • Barker, J.E.1    Ren, T.2
  • 33
    • 67349169066 scopus 로고    scopus 로고
    • Thioanisole oxidation with hydrogen peroxide catalyzed by hexadentate 8-quinolinolato manganese(III) complexes
    • Xie, F.; Fu, Z. H.; Zhong, S.; Ye, Z. P.; Zhou, X. P.; Liu, F. L.; Rong, C. Y.; Mao, L. Q.; Yin, D. L. Thioanisole Oxidation with Hydrogen Peroxide Catalyzed by Hexadentate 8-Quinolinolato Manganese(III) Complexes. J. Mol. Catal. A 2009, 307, 93.
    • (2009) J. Mol. Catal. A , vol.307 , pp. 93
    • Xie, F.1    Fu, Z.H.2    Zhong, S.3    Ye, Z.P.4    Zhou, X.P.5    Liu, F.L.6    Rong, C.Y.7    Mao, L.Q.8    Yin, D.L.9
  • 34
    • 0035503830 scopus 로고    scopus 로고
    • Enantioselective oxidation of sulfide to sulfoxide on Ti-containing mesoporous silica prepared by a template-ion exchange method
    • Iwamoto, M.; Tanaka, Y.; Hirosumi, J.; Kita, N.; Triwahyono, S. Enantioselective Oxidation of Sulfide to Sulfoxide on Ti-containing Mesoporous Silica Prepared by a Template-ion Exchange Method. Microporous Mesoporous Mater. 2001, 48, 271.
    • (2001) Microporous Mesoporous Mater. , vol.48 , pp. 271
    • Iwamoto, M.1    Tanaka, Y.2    Hirosumi, J.3    Kita, N.4    Triwahyono, S.5
  • 35
    • 33846213882 scopus 로고    scopus 로고
    • Ultrasound-accelerated green and selective oxidation of sulfides to sulfoxides
    • Mahamuni, N. N.; Gogate, P. R.; Pandit, A. B. Ultrasound-Accelerated Green and Selective Oxidation of Sulfides to Sulfoxides. Ind. Eng. Chem. Res. 2006, 45, 8829.
    • (2006) Ind. Eng. Chem. Res. , vol.45 , pp. 8829
    • Mahamuni, N.N.1    Gogate, P.R.2    Pandit, A.B.3
  • 36
    • 33646527589 scopus 로고    scopus 로고
    • Efficient and selective sulfoxidation by hydrogen peroxide, using a recyclable flavin [BMIm]PF6 catalytic system
    • Lindén, A. A.; Johansson, M.; Hermanns, N.; Bäckvall, J. E. Efficient and Selective Sulfoxidation by Hydrogen Peroxide, Using a Recyclable Flavin [BMIm]PF6 Catalytic System. J. Org. Chem. 2006, 71, 3849.
    • (2006) J. Org. Chem. , vol.71 , pp. 3849
    • Lindén, A.A.1    Johansson, M.2    Hermanns, N.3    Bäckvall, J.E.4
  • 37
    • 0001477475 scopus 로고
    • Mechanism of the oxidation of p,p′-dichlorobenzyl sulfide by peroxybenzoic and para substituted peroxybenzoic acids
    • Overberger, C. G.; Cumrnins, R. W. Mechanism of the Oxidation of p,p′-Dichlorobenzyl Sulfide by Peroxybenzoic and para Substituted Peroxybenzoic Acids. J. Am. Chem. Soc. 1953, 75, 4250.
    • (1953) J. Am. Chem. Soc. , vol.75 , pp. 4250
    • Overberger, C.G.1    Cumrnins, R.W.2
  • 38
    • 33947477752 scopus 로고
    • The kinetics of the oxidation of thiodiethanol by t-Butyl hydroperoxide
    • Edwards, J. O.; Fortnum, D. H. The Kinetics of the Oxidation of Thiodiethanol by t-Butyl Hydroperoxide. J. Org. Chem. 1962, 27, 407.
    • (1962) J. Org. Chem. , vol.27 , pp. 407
    • Edwards, J.O.1    Fortnum, D.H.2
  • 39
    • 0000846868 scopus 로고
    • The mechanism of the oxidation of some aromatic amines by peroxyacetic acid
    • Ibne-Rasa, K. M.; Edwards, J. O. The Mechanism of the Oxidation of Some Aromatic Amines by Peroxyacetic Acid. J. Am. Chem. Soc. 1962, 84, 763.
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 763
    • Ibne-Rasa, K.M.1    Edwards, J.O.2
  • 40
    • 0347196791 scopus 로고
    • Mechanism of the oxidation of nitrosobenzenes by peroxoacetic acid
    • Ibne-Rasa, K. M.; Lauro, C. G.; Edwards, J. O. Mechanism of the Oxidation of Nitrosobenzenes by Peroxoacetic Acid. J. Am. Chem. Soc. 1963, 85, 1165.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 1165
    • Ibne-Rasa, K.M.1    Lauro, C.G.2    Edwards, J.O.3
  • 41
    • 33947323728 scopus 로고
    • The influence of solvent on the oxidation of thioxane by hydrogen peroxide and by tert-butyl hydroperoxide
    • Dankleff, M. A. P.; Ruggero, C.; Edwards, J. O.; Pyun, H. Y. The Influence of Solvent on The Oxidation of Thioxane by Hydrogen Peroxide and by Tert-butyl Hydroperoxide. J. Am. Chem. Soc. 1968, 90, 3209.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 3209
    • Dankleff, M.A.P.1    Ruggero, C.2    Edwards, J.O.3    Pyun, H.Y.4


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