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Aerobic oxidation of thiols to disulfides by heterogeneous gold catalysts

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Aerobic oxidation of thiols to disulfides by heterogeneous gold catalysts

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dc.contributor.author Corma Canós, Avelino es_ES
dc.contributor.author Ródenas Torralba, Tania es_ES
dc.contributor.author Sabater Picot, Mª José es_ES
dc.date.accessioned 2016-04-11T10:43:32Z
dc.date.available 2016-04-11T10:43:32Z
dc.date.issued 2012
dc.identifier.issn 2041-6520
dc.identifier.uri http://hdl.handle.net/10251/62415
dc.description.abstract Thiols are smoothly and efficiently oxidized to disulfides (RSSR) with air in the presence of gold nanoparticles supported on CeO2 in absence of solvent, as well as in aqueous solutions and neutral pH. It is shown that the reaction can occur through the coupling of two sulphur radicals on the metal surface. The sulphur radicals are formed from thiols by one-electron oxidation with the metal. This reaction mechanism strongly resembles that found for sulfhydryl oxidases, a class of enzymes which are involved in the oxidative protein folding through de novo formation of disulfides from thiols. es_ES
dc.description.sponsorship lFinancial support by Consolider-Ingenio 2010 (project MULTICAT), Spanish MICINN (Projects MAT2006-14274-C02-01 and MAT2011-28009), Generalitat Valenciana (Project PROMETEO/2008/130) and Fundacion Areces are gratefully acknowledged. T.R. expresses her gratitude to Consejo Superior de Investigaciones Cientificas for an I3-P fellowship. en_EN
dc.language Inglés es_ES
dc.publisher Royal Society of Chemistry es_ES
dc.relation.ispartof Chemical Science es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject MOLECULAR-OXYGEN es_ES
dc.subject AIR OXIDATION es_ES
dc.subject SILICA-GEL es_ES
dc.subject C-C es_ES
dc.subject EFFICIENT es_ES
dc.subject BONDS es_ES
dc.subject MILD es_ES
dc.subject ACID es_ES
dc.subject PERMANGANATE es_ES
dc.subject COBALT(II) es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Aerobic oxidation of thiols to disulfides by heterogeneous gold catalysts es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c1sc00466b
dc.relation.projectID info:eu-repo/grantAgreement/MEC//MAT2006-14274-C02-01/ES/DISEÑO MOLECULAR DE NANOMATERIALES ESTRUCTURADOS ORGANICOS-INORGANICOS PARA SU APLICACION EN CATALISIS, SEPARACION DE GASES Y BIOMEDICA./ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Generalitat Valenciana//PROMETEO08%2F2008%2F130/ES/Química sostenible: Catalizadores moleculares y supramoleculares altamente selectivos, estables y energéticamente eficientes en reacciones químicas./ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Corma Canós, A.; Ródenas Torralba, T.; Sabater Picot, MJ. (2012). Aerobic oxidation of thiols to disulfides by heterogeneous gold catalysts. Chemical Science. 3(2):398-404. https://doi.org/10.1039/c1sc00466b es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1039/c1sc00466b es_ES
dc.description.upvformatpinicio 398 es_ES
dc.description.upvformatpfin 404 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 3 es_ES
dc.description.issue 2 es_ES
dc.relation.senia 214215 es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Ministerio de Educación y Ciencia es_ES
dc.contributor.funder Fundación Ramón Areces es_ES
dc.contributor.funder Consejo Superior de Investigaciones Científicas es_ES
dc.description.references Block, E. (1992). The Organosulfur Chemistry of the GenusAllium - Implications for the Organic Chemistry of Sulfur. Angewandte Chemie International Edition in English, 31(9), 1135-1178. doi:10.1002/anie.199211351 es_ES
dc.description.references Kanda, Y., & Fukuyama, T. (1993). Total synthesis of (+)-leinamycin. Journal of the American Chemical Society, 115(18), 8451-8452. doi:10.1021/ja00071a066 es_ES
dc.description.references Gilbert, H. F. (1995). [2] Thiol/disulfide exchange equilibria and disulfidebond stability. Biothiols Part A Monothiols and Dithiols, Protein Thiols, and Thiyl Radicals, 8-28. doi:10.1016/0076-6879(95)51107-5 es_ES
dc.description.references Eckardt, N. A. (2006). Ferredoxin-Thioredoxin System Plays a Key Role in Plant Response to Oxidative Stress. The Plant Cell, 18(8), 1782-1782. doi:10.1105/tpc.106.180810 es_ES
dc.description.references Balmer, Y., Vensel, W. H., Cai, N., Manieri, W., Schurmann, P., Hurkman, W. J., & Buchanan, B. B. (2006). A complete ferredoxin/thioredoxin system regulates fundamental processes in amyloplasts. Proceedings of the National Academy of Sciences, 103(8), 2988-2993. doi:10.1073/pnas.0511040103 es_ES
dc.description.references Swaisgood, H. E. (2005). The importance of disulfide bridging. Biotechnology Advances, 23(1), 71-73. doi:10.1016/j.biotechadv.2004.09.004 es_ES
dc.description.references Visschers, R. W., & de Jongh, H. H. J. (2005). Disulphide bond formation in food protein aggregation and gelation. Biotechnology Advances, 23(1), 75-80. doi:10.1016/j.biotechadv.2004.09.005 es_ES
dc.description.references Bulaj, G. (2005). Formation of disulfide bonds in proteins and peptides. Biotechnology Advances, 23(1), 87-92. doi:10.1016/j.biotechadv.2004.09.002 es_ES
dc.description.references Kühle, E., & Klauke, E. (1977). Fluorinated Isocyanates and Their Derivatives as Intermediates for Biologically Active Compounds. Angewandte Chemie International Edition in English, 16(11), 735-742. doi:10.1002/anie.197707353 es_ES
dc.description.references Firouzabadi, H., Iranpoor, N., Parham, H., Sardarian, A., & Toofan, J. (1984). Oxidation of Thiols to Their Disulfides with Bis Trinitratocerium (IV)l Chromate [Ce(NO3)312CrO4and Pyridinum Chlorochromate. Synthetic Communications, 14(8), 717-724. doi:10.1080/00397918408059586 es_ES
dc.description.references Firouzabadi, H., Naderi, M., Sardarian, A., & Vessal, B. (1983). The Facile Oxidation of Thiols to Disulfides with Bis(2,2′-Bipyridyl) Copper-(II) Permanganate. Synthetic Communications, 13(7), 611-615. doi:10.1080/00397918308059536 es_ES
dc.description.references Noureldin, N. A., Caldwell, M., Hendry, J., & Lee, D. G. (1998). Heterogeneous Permanganate Oxidation of Thiols. Synthesis, 1998(11), 1587-1589. doi:10.1055/s-1998-2190 es_ES
dc.description.references Wallace, T. J. (1966). Reactions of Thiols with Metals. I. Low-Temperature Oxidation by Metal Oxides1. The Journal of Organic Chemistry, 31(4), 1217-1221. doi:10.1021/jo01342a056 es_ES
dc.description.references Firouzabadi, H., Iranpoor, N., Kiaeezadeh, F., & Toofan, J. (1986). Chromium(VI) based oxidants-1. Tetrahedron, 42(2), 719-725. doi:10.1016/s0040-4020(01)87476-7 es_ES
dc.description.references McKillop, A., Koyunçu, D., Krief, A., Dumont, W., Renier, P., & Trabelsi, M. (1990). Efficicient, high yield, oxidation of thiols and selenols to disulphides and diselenides. Tetrahedron Letters, 31(35), 5007-5010. doi:10.1016/s0040-4039(00)97790-6 es_ES
dc.description.references Ramesha, A. R., & Chandrasekaran, S. (1994). A facile entry to macrocyclic disulfides: an efficient synthesis of redox-switched crown ethers. The Journal of Organic Chemistry, 59(6), 1354-1357. doi:10.1021/jo00085a025 es_ES
dc.description.references Ramadas, K., & Srinivasan, N. (1995). Sodium Chlorite - Yet Another Oxidant for Thiols to Disulphides. Synthetic Communications, 25(2), 227-234. doi:10.1080/00397919508010811 es_ES
dc.description.references Pryor, W. A., Church, D. F., Govindan, C. K., & Crank, G. (1982). Oxidation of thiols by nitric oxide and nitrogen dioxide: synthetic utility and toxicological implications. The Journal of Organic Chemistry, 47(1), 156-159. doi:10.1021/jo00340a038 es_ES
dc.description.references Iranpoor, N., Firouzabadi, H., & Zolfigol, M. A. (1998). Dinitrogen Tetroxide Copper Nitrate Complex [Cu(NO3)2.N2O4] As a New Nitrosating Agent for Catalytic Coupling of Thiols via Thionitrite. Synthetic Communications, 28(2), 367-375. doi:10.1080/00397919808005729 es_ES
dc.description.references Wu, X., Rieke, R. D., & Zhu, L. (1996). Preparation of Disulfides by the Oxidation of Thiols Using Bromine. Synthetic Communications, 26(1), 191-196. doi:10.1080/00397919608003879 es_ES
dc.description.references Ali, M. H., & McDermott, M. (2002). Oxidation of thiols to disulfides with molecular bromine on hydrated silica gel support. Tetrahedron Letters, 43(35), 6271-6273. doi:10.1016/s0040-4039(02)01220-0 es_ES
dc.description.references Khazaei, A., Zolfigol, M. A., & Rostami, A. (2004). 1,3-Dibromo-5,5-Dimethylhydantoin [DBDMH] as an Efficient and Selective Agent for the Oxidation of Thiols to Disulfides in Solution or under Solvent-Free Conditions. Synthesis, (18), 2959-2961. doi:10.1055/s-2004-834919 es_ES
dc.description.references Joshi, A. V., Bhusare, S., Baidossi, M., Qafisheh, N., & Sasson, Y. (2005). Oxidative coupling of thiols to disulfides using a solid anhydrous potassium phosphate catalyst. Tetrahedron Letters, 46(20), 3583-3585. doi:10.1016/j.tetlet.2005.03.040 es_ES
dc.description.references Patel, S., & Mishra, B. K. (2004). Cetyltrimethylammonium dichromate: a mild oxidant for coupling amines and thiols. Tetrahedron Letters, 45(7), 1371-1372. doi:10.1016/j.tetlet.2003.12.068 es_ES
dc.description.references Leino, R., & Lönnqvist, J.-E. (2004). A very simple method for the preparation of symmetrical disulfides. Tetrahedron Letters, 45(46), 8489-8491. doi:10.1016/j.tetlet.2004.09.100 es_ES
dc.description.references Delaude, L., & Laszlo, P. (1996). A Novel Oxidizing Reagent Based on Potassium Ferrate(VI)1. The Journal of Organic Chemistry, 61(18), 6360-6370. doi:10.1021/jo960633p es_ES
dc.description.references Peskin, A. V., & Winterbourn, C. C. (2001). Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate. Free Radical Biology and Medicine, 30(5), 572-579. doi:10.1016/s0891-5849(00)00506-2 es_ES
dc.description.references Akdag, A., Webb, T., & Worley, S. D. (2006). Oxidation of thiols to disulfides with monochloro poly(styrenehydantoin) beads. Tetrahedron Letters, 47(21), 3509-3510. doi:10.1016/j.tetlet.2006.03.105 es_ES
dc.description.references Kirihara, M., Asai, Y., Ogawa, S., Noguchi, T., Hatano, A., & Hirai, Y. (2007). A Mild and Environmentally Benign Oxidation of Thiols to Disulfides. Synthesis, 2007(21), 3286-3289. doi:10.1055/s-2007-990800 es_ES
dc.description.references LIU, K.-T., & TONG, Y.-C. (1978). A Facile Conversion of Thiols to Disulfides. Synthesis, 1978(09), 669-670. doi:10.1055/s-1978-24844 es_ES
dc.description.references Rao, T. V., Sain, B., Murthy, P. S., Rao, T. S. R. P., Joshi, G. C., & Jain, A. K. (1997). Iron(III )–Ethylenediaminetetraacetic AcidMediated Oxidation of Thiols to Disulfides with MolecularOxygen†. Journal of Chemical Research, (8), 300-301. doi:10.1039/a702061i es_ES
dc.description.references Walters, M. A., Chaparro, J., Siddiqui, T., Williams, F., Ulku, C., & Rheingold, A. L. (2006). The formation of disulfides by the [Fe(nta)Cl2]2− catalyzed air oxidation of thiols and dithiols. Inorganica Chimica Acta, 359(12), 3996-4000. doi:10.1016/j.ica.2006.03.043 es_ES
dc.description.references Rao, T. V., Rao, K. N., Jain, S. L., & Sain, B. (2002). COBALT PHTHALOCYANINE MEDIATED AEROBIC OXIDATION OF THIOLS: A SIMPLE AND CONVENIENT PREPARATION OF DISULPHIDES. Synthetic Communications, 32(8), 1151-1157. doi:10.1081/scc-120003604 es_ES
dc.description.references Simándi, L. I., Németh, S., & Rumelis, N. (1987). Cobalt(II) ion catalyzed oxidation of o-substituted anilines with molecular oxygen. Journal of Molecular Catalysis, 42(3), 357-360. doi:10.1016/0304-5102(87)85011-3 es_ES
dc.description.references S. Uemura , Comprehensive Organic Synthesis, B. M. Trost, I. Fleming Ed., Pergamon Press, New York, 1991, Vol 7., 757 es_ES
dc.description.references Hashemi, M. M., & Karimi-Jaberi, Z. (2004). Oxidation of Thiols to Disulfides by Oxygen in Presence of Cobalt(II) and Manganese(II) Salts of 4-Aminobenzoic Acid Supported on Silica Gel. Monatshefte f�r Chemie / Chemical Monthly, 135(1), 41-43. doi:10.1007/s00706-003-0102-5 es_ES
dc.description.references Cervilla, A., Corma, A., Fornes, V., Llopis, E., Palanca, P., Rey, F., & Ribera, A. (1994). Intercalation of [MoVIO2(O2CC(S)Ph2)2]2- in a Zn(II)-Al(III) Layered Double Hydroxide Host: A Strategy for the Heterogeneous Catalysis of the Air Oxidation of Thiols. Journal of the American Chemical Society, 116(4), 1595-1596. doi:10.1021/ja00083a065 es_ES
dc.description.references Saxena, A., Kumar, A., & Mozumdar, S. (2007). Ni-nanoparticles: An efficient green catalyst for chemo-selective oxidative coupling of thiols. Journal of Molecular Catalysis A: Chemical, 269(1-2), 35-40. doi:10.1016/j.molcata.2006.12.042 es_ES
dc.description.references Corma, A., Leyva-Pérez, A., & Sabater, M. J. (2011). Gold-Catalyzed Carbon−Heteroatom Bond-Forming Reactions. Chemical Reviews, 111(3), 1657-1712. doi:10.1021/cr100414u es_ES
dc.description.references Arcadi, A. (2008). Alternative Synthetic Methods through New Developments in Catalysis by Gold. Chemical Reviews, 108(8), 3266-3325. doi:10.1021/cr068435d es_ES
dc.description.references Hashmi, A. S. K. (2007). Gold-Catalyzed Organic Reactions. Chemical Reviews, 107(7), 3180-3211. doi:10.1021/cr000436x es_ES
dc.description.references Gorin, D. J., Sherry, B. D., & Toste, F. D. (2008). Ligand Effects in Homogeneous Au Catalysis. Chemical Reviews, 108(8), 3351-3378. doi:10.1021/cr068430g es_ES
dc.description.references Fürstner, A. (2009). Gold and platinum catalysis—a convenient tool for generating molecular complexity. Chemical Society Reviews, 38(11), 3208. doi:10.1039/b816696j es_ES
dc.description.references Shen, H. C. (2008). Recent advances in syntheses of heterocycles and carbocycles via homogeneous gold catalysis. Part 1: Heteroatom addition and hydroarylation reactions of alkynes, allenes, and alkenes. Tetrahedron, 64(18), 3885-3903. doi:10.1016/j.tet.2008.01.081 es_ES
dc.description.references Hashmi, A. S. K., & Rudolph, M. (2008). Gold catalysis in total synthesis. Chemical Society Reviews, 37(9), 1766. doi:10.1039/b615629k es_ES
dc.description.references Muzart, J. (2008). Gold-catalysed reactions of alcohols: isomerisation, inter- and intramolecular reactions leading to C–C and C–heteroatom bonds. Tetrahedron, 64(25), 5815-5849. doi:10.1016/j.tet.2008.04.018 es_ES
dc.description.references Hutchings, G. J. (2008). Supported gold and gold palladium catalysts for selective chemical synthesis. Catalysis Today, 138(1-2), 9-14. doi:10.1016/j.cattod.2008.04.029 es_ES
dc.description.references Widenhoefer, R. A., & Han, X. (2006). Gold-Catalyzed Hydroamination of C–C Multiple Bonds. European Journal of Organic Chemistry, 2006(20), 4555-4563. doi:10.1002/ejoc.200600399 es_ES
dc.description.references Haruta, M. (1997). Size- and support-dependency in the catalysis of gold. Catalysis Today, 36(1), 153-166. doi:10.1016/s0920-5861(96)00208-8 es_ES
dc.description.references Haruta, M. (1997). Catalysis Surveys from Japan, 1(1), 61-73. doi:10.1023/a:1019068728295 es_ES
dc.description.references A. Corma , H.Garcia, Supported gold nanoparticles as oxidation catalysts from Nanoparticles and Catalysis, 2008, 389. Editor: D. Astruc es_ES
dc.description.references C. Della Pina , E.Falletta, M.Rossi, Gold nanoparticles-catalyzed oxidations in organic chemistry, ibid, p. 427 es_ES
dc.description.references C. Louis , Gold nanoparticles: recent advances in CO oxidation, ibid, pp. 475–503 es_ES
dc.description.references Carrettin, S., Concepción, P., Corma, A., López Nieto, J. M., & Puntes, V. F. (2004). Nanocrystalline CeO2 Increases the Activity of Au for CO Oxidation by Two Orders of Magnitude. Angewandte Chemie International Edition, 43(19), 2538-2540. doi:10.1002/anie.200353570 es_ES
dc.description.references Budroni, G., & Corma, A. (2006). Gold–Organic–Inorganic High-Surface-Area Materials as Precursors of Highly Active Catalysts. Angewandte Chemie International Edition, 45(20), 3328-3331. doi:10.1002/anie.200600552 es_ES
dc.description.references The pair reduced l-glutathione/oxidized l-glutathione (G–SH/G–SS–G) is the major intracellular redox buffer es_ES
dc.description.references Zhang, X., & Corma, A. (2008). Supported Gold(III) Catalysts for Highly Efficient Three-Component Coupling Reactions. Angewandte Chemie International Edition, 47(23), 4358-4361. doi:10.1002/anie.200800098 es_ES
dc.description.references Jenner, E. L., & Lindsey, R. V. (1961). Syntheses by Free-radical Reactions. XIII. Reactions of Thiyl Radicals with Olefins. Journal of the American Chemical Society, 83(8), 1911-1915. doi:10.1021/ja01469a031 es_ES
dc.description.references Handbook of Chemistry and Physics, 82nd ed. CRC Press, New York, 2001, p 9–52–9–63 es_ES
dc.description.references Buettner, G. R. (1987). Spin Trapping: ESR parameters of spin adducts 1474 1528V. Free Radical Biology and Medicine, 3(4), 259-303. doi:10.1016/s0891-5849(87)80033-3 es_ES
dc.description.references Grirrane, A., Corma, A., & Garcia, H. (2008). Gold-Catalyzed Synthesis of Aromatic Azo Compounds from Anilines and Nitroaromatics. Science, 322(5908), 1661-1664. doi:10.1126/science.1166401 es_ES
dc.description.references Cullis, C. F., Hopton, J. D., Swan, C. J., & Trimm, D. L. (2007). Oxidation of thiols in gas-liquid systems. II. Reaction in the presence of added metal catalysts. Journal of Applied Chemistry, 18(11), 335-339. doi:10.1002/jctb.5010181105 es_ES
dc.description.references the amount of water formed was estimated by the Karl-Fisher method es_ES
dc.description.references Collet, J.-F., & Bardwell, J. C. A. (2002). Disulfides out of thin air. Nature Structural Biology, 9(1), 2-3. doi:10.1038/nsb0102-2 es_ES


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