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Tetrahydropyranyl Protection and Deprotection of Alcohols using Niobium Phosphate as a Brønsted Acid Catalyst

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Tetrahydropyranyl Protection and Deprotection of Alcohols using Niobium Phosphate as a Brønsted Acid Catalyst

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Crites, CL.; Lima, FM.; Marín García, ML.; Netto Ferreira, JC.; Impellizzeri, S.; Hallett-Tapley, GL.; Scaiano, JC. (2016). Tetrahydropyranyl Protection and Deprotection of Alcohols using Niobium Phosphate as a Brønsted Acid Catalyst. Canadian Journal of Chemistry. 94(8):712-714. doi:10.1139/cjc-2015-0538

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Título: Tetrahydropyranyl Protection and Deprotection of Alcohols using Niobium Phosphate as a Brønsted Acid Catalyst
Autor: Crites, Charles-Oneil L. Lima, Filipe Matos Marín García, Mª Luisa Netto Ferreira, Jose Carlos Impellizzeri, Stefania Hallett-Tapley, Geniece L. Scaiano, Juan César
Entidad UPV: Universitat Politècnica de València. Escuela Técnica Superior de Ingenieros Industriales - Escola Tècnica Superior d'Enginyers Industrials
Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química
Fecha difusión:
Resumen:
Solid niobium oxide treated with phosphoric acid (NbP) was used as a heterogeneous catalyst in the protection of a series of aliphatic alcohols as tetrahydropyranyl (THP) derivatives. Protection of primary alcohols using ...[+]
Palabras clave: catalysis , niobium , deprotection , Bronsted acid
Derechos de uso: Reserva de todos los derechos
Fuente:
Canadian Journal of Chemistry. (issn: 0008-4042 ) (eissn: 1480-3291 )
DOI: 10.1139/cjc-2015-0538
Editorial:
NRC Research Press (Canadian Science Publishing)
Versión del editor: http://doi.org/10.1139/cjc-2015-0538
Tipo: Artículo

References

Parham, W. E., & Anderson, E. L. (1948). The Protection of Hydroxyl Groups. Journal of the American Chemical Society, 70(12), 4187-4189. doi:10.1021/ja01192a062

Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 3rd ed. John Wiley & Sons, Inc.: New York, 1999.

Stephens, J. R., Butler, P. L., Clow, C. H., Oswald, M. C., Smith, R. C., & Mohan, R. S. (2003). Bismuth Triflate: An Efficient Catalyst for the Formation and Deprotection of Tetrahydropyranyl Ethers. European Journal of Organic Chemistry, 2003(19), 3827-3831. doi:10.1002/ejoc.200300295 [+]
Parham, W. E., & Anderson, E. L. (1948). The Protection of Hydroxyl Groups. Journal of the American Chemical Society, 70(12), 4187-4189. doi:10.1021/ja01192a062

Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; 3rd ed. John Wiley & Sons, Inc.: New York, 1999.

Stephens, J. R., Butler, P. L., Clow, C. H., Oswald, M. C., Smith, R. C., & Mohan, R. S. (2003). Bismuth Triflate: An Efficient Catalyst for the Formation and Deprotection of Tetrahydropyranyl Ethers. European Journal of Organic Chemistry, 2003(19), 3827-3831. doi:10.1002/ejoc.200300295

VAN Boom, J. H., HERSCHIED, J. D. M., & REESE, C. B. (1973). p-Toluenesulfonic Acid as a Catalyst for the Rapid Tetrahydropyranylation and Methoxytetrahydropyranylation of Steroidal Alcohols. Synthesis, 1973(03), 169-170. doi:10.1055/s-1973-22165

Miyashita, M., Yoshikoshi, A., & Grieco, P. A. (1977). Pyridinium p-toluenesulfonate. A mild and efficient catalyst for the tetrahydropyranylation of alcohols. The Journal of Organic Chemistry, 42(23), 3772-3774. doi:10.1021/jo00443a038

Bhalerao, U. T., Davis, K. J., & Rao, B. V. (1996). Copper(II)chloride Catalyzed Tetrahydropyranylation of Alcohols. Synthetic Communications, 26(16), 3081-3085. doi:10.1080/00397919608004611

Bongini, A., Cardillo, G., Orena, M., & Sandri, S. (1979). A Simple and Practical Method for Tetrahydropyranylation of Alcohols and Phenols. Synthesis, 1979(08), 618-620. doi:10.1055/s-1979-28784

Upadhya, T. T., Daniel, T., Sudalai, A., Ravindranathan, T., & Sabu, K. R. (1996). Natural Kaolinitic Clay: A Mild and Efficient Catalyst for the Tetrahydropyranylation and Trimethylsilylation of Alcohols. Synthetic Communications, 26(24), 4539-4544. doi:10.1080/00397919608004777

Campelo, J. M., Garcia, A., Lafont, F., Luna, D., & Marinas, J. M. (1994). Spanish Sepiolite Clay as a New Heterogeneous Catalyst for the Tetrahydropyranylation of Alcohols and Phenols. Synthetic Communications, 24(10), 1345-1350. doi:10.1080/00397919408011737

Kumar, P., Dinesh, C. U., Reddy, R. S., & Pandey, B. (1993). H-Y Zeolite: A Mild and Efficient Catalyst for the Tetrahydropyranylation of Alcohols. Synthesis, 1993(11), 1069-1070. doi:10.1055/s-1993-25998

Ranu, B. C., & Saha, M. (1994). A Simple, Efficient, and Selective Method for Tetrahydropyranylation of Alcohols on a Solid Phase of Alumina Impregnated with Zinc Chloride. The Journal of Organic Chemistry, 59(26), 8269-8270. doi:10.1021/jo00105a054

Liu, J., & Wong, C.-H. (2002). An efficient method for the cleavage of p-methoxybenzylidene (PMP), tetrahydropyranyl (THP) and 1,3-dithiane protecting groups by Selectfluor™. Tetrahedron Letters, 43(22), 4037-4039. doi:10.1016/s0040-4039(02)00740-2

Wang, J., Zhang, C., Qu, Z., Hou, Y., Chen, B., & Wu, P. (1999). Copper(II) Chloride Dihydrate: A Catalytic Agent for the Deprotection of Tetrahydropyranyl Ethers (THP Ethers) and 1-Ethoxyethyl Ethers (EE Ethers). Journal of Chemical Research, (4), 294-295. doi:10.1039/a900262f

Hoyer, S., Laszlo, P., Orlović, M., & Polla, E. (1986). Catalysis by Acidic Clay of the Protective Tetrahydropyranylation of Alcohols and Phenols. Synthesis, 1986(08), 655-657. doi:10.1055/s-1986-31736

Sartori, G., Ballini, R., Bigi, F., Bosica, G., Maggi, R., & Righi, P. (2004). Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis. Chemical Reviews, 104(1), 199-250. doi:10.1021/cr0200769

CARNITI, P., GERVASINI, A., BIELLA, S., & AUROUX, A. (2006). Niobic acid and niobium phosphate as highly acidic viable catalysts in aqueous medium: Fructose dehydration reaction. Catalysis Today, 118(3-4), 373-378. doi:10.1016/j.cattod.2006.07.024

Bassan, I. A. L., Nascimento, D. R., San Gil, R. A. S., da Silva, M. I. P., Moreira, C. R., Gonzalez, W. A., … Lachter, E. R. (2013). Esterification of fatty acids with alcohols over niobium phosphate. Fuel Processing Technology, 106, 619-624. doi:10.1016/j.fuproc.2012.09.054

Reis, M. C., Barros, S. D. T., Lachter, E. R., San Gil, R. A. S., Flores, J. H., Pais da Silva, M. I., & Onfroy, T. (2012). Synthesis, characterization and catalytic activity of meso-niobium phosphate in the oxidation of benzyl alcohols. Catalysis Today, 192(1), 117-122. doi:10.1016/j.cattod.2012.05.025

Rocha, A. S., Forrester, A. M. S., de la Cruz, M. H. C., da Silva, C. T., & Lachter, E. R. (2008). Comparative performance of niobium phosphates in liquid phase anisole benzylation with benzyl alcohol. Catalysis Communications, 9(10), 1959-1965. doi:10.1016/j.catcom.2008.03.019

Impellizzeri, S., Simoncelli, S., Fasciani, C., Luisa Marin, M., Hallett-Tapley, G. L., Hodgson, G. K., & Scaiano, J. C. (2015). Mechanistic insights into the Nb2O5 and niobium phosphate catalyzed in situ condensation of a fluorescent halochromic assembly. Catalysis Science & Technology, 5(1), 169-175. doi:10.1039/c4cy00703d

Den Boer, A. W., & Malakhov, D. V. (2014). Critical role of carbon during production of ferroniobium alloy additions. Canadian Metallurgical Quarterly, 53(4), 423-431. doi:10.1179/1879139514y.0000000134

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