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Sweet chiral porphyrins as singlet oxygen sensitizers for asymmetric Type II photooxygenation

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Sweet chiral porphyrins as singlet oxygen sensitizers for asymmetric Type II photooxygenation

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Griesbeck, AG.; Miranda Alonso, MÁ.; Uhlig, J. (2011). Sweet chiral porphyrins as singlet oxygen sensitizers for asymmetric Type II photooxygenation. Photochemical & Photobiological Sciences Photochemical and Photobiological Sciences. 10(9):1431-1435. doi:10.1039/c1pp05052d

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Título: Sweet chiral porphyrins as singlet oxygen sensitizers for asymmetric Type II photooxygenation
Autor: Griesbeck, Axel G. Miranda Alonso, Miguel Ángel Uhlig, Johannes
Entidad UPV: Universitat Politècnica de València. Departamento de Química - Departament de Química
Fecha difusión:
Resumen:
Carbohydrate-decorated meso-tetraarylporphyrins P-G and P-C were synthesized via Lewis-acid catalyzed condensation of acetylated carbohydrate-substituted benzaldehydes and pyrrole. Their efficiency of singlet oxygen ...[+]
Palabras clave: CYCLODEXTRIN-SANDWICHED PORPHYRIN , POLYSTYRENE BEADS , MOLECULAR-OXYGEN , METHYLENE-BLUE , PHOTOOXIDATION , OXIDATION , SULFIDES , PHOTOSENSITIZERS , PHOTOCHEMISTRY , CONVENIENT
Derechos de uso: Cerrado
Fuente:
Photochemical & Photobiological Sciences Photochemical and Photobiological Sciences. (issn: 1474-905X )
DOI: 10.1039/c1pp05052d
Editorial:
Royal Society of Chemistry
Versión del editor: http://dx.doi.org/10.1039/c1pp05052d
Agradecimientos:
The financial support by the Deutsche Forschungsgemeinschaft (DFG) is acknowledged. J.U. thanks the Alder foundation for a half-year research stay in Valencia.
Tipo: Artículo

References

Noyori, R., Aoki, M., & Sato, K. (2003). Green oxidation with aqueous hydrogen peroxide. Chemical Communications, (16), 1977. doi:10.1039/b303160h

Adam, W., Braun, M., Griesbeck, A., Lucchini, V., Staab, E., & Will, B. (1989). Photooxygenation of olefins in the presence of titanium(IV) catalyst. A convienient «one-pot» synthesis of epoxy alcohols. Journal of the American Chemical Society, 111(1), 203-212. doi:10.1021/ja00183a032

Kuimova, M. K., Yahioglu, G., & Ogilby, P. R. (2009). Singlet Oxygen in a Cell: Spatially Dependent Lifetimes and Quenching Rate Constants. Journal of the American Chemical Society, 131(1), 332-340. doi:10.1021/ja807484b [+]
Noyori, R., Aoki, M., & Sato, K. (2003). Green oxidation with aqueous hydrogen peroxide. Chemical Communications, (16), 1977. doi:10.1039/b303160h

Adam, W., Braun, M., Griesbeck, A., Lucchini, V., Staab, E., & Will, B. (1989). Photooxygenation of olefins in the presence of titanium(IV) catalyst. A convienient «one-pot» synthesis of epoxy alcohols. Journal of the American Chemical Society, 111(1), 203-212. doi:10.1021/ja00183a032

Kuimova, M. K., Yahioglu, G., & Ogilby, P. R. (2009). Singlet Oxygen in a Cell: Spatially Dependent Lifetimes and Quenching Rate Constants. Journal of the American Chemical Society, 131(1), 332-340. doi:10.1021/ja807484b

Schweitzer, C., & Schmidt, R. (2003). Physical Mechanisms of Generation and Deactivation of Singlet Oxygen. Chemical Reviews, 103(5), 1685-1758. doi:10.1021/cr010371d

Schaap, A. P., Thayer, A. L., Blossey, E. C., & Neckers, D. C. (1975). Polymer-based sensitizers for photooxidations. II. Journal of the American Chemical Society, 97(13), 3741-3745. doi:10.1021/ja00846a030

Jensen, A. W., & Daniels, C. (2003). Fullerene-Coated Beads as Reusable Catalysts. The Journal of Organic Chemistry, 68(2), 207-210. doi:10.1021/jo025926z

Johnson Inbaraj, J., Vinodu, M. V., Gandhidasan, R., Murugesan, R., & Padmanabhan, M. (2003). Photosensitizing properties of ionic porphyrins immobilized on functionalized solid polystyrene support. Journal of Applied Polymer Science, 89(14), 3925-3930. doi:10.1002/app.12610

Benaglia, M., Danelli, T., Fabris, F., Sperandio, D., & Pozzi, G. (2002). Poly(ethylene glycol)-Supported Tetrahydroxyphenyl Porphyrin:  A Convenient, Recyclable Catalyst for Photooxidation Reactions. Organic Letters, 4(24), 4229-4232. doi:10.1021/ol0267230

Bourdelande, J. L., Font, J., & Sánchez-Ferrando, F. (1983). The use of insoluble benzoylated polystyrene beads (polymeric benzophenone) in photochemical reactions. Canadian Journal of Chemistry, 61(5), 1007-1016. doi:10.1139/v83-178

Mattay, J., Vondenhof, M., & Denig, R. (1989). Pyrylium Salts as Photosensitizers in Homogeneous and Heterogeneous Electron-Transfer Catalysis. – A Comparison with Cyano Arenes. Chemische Berichte, 122(5), 951-958. doi:10.1002/cber.19891220526

Zhang, D., Wu, L.-Z., Yang, Q.-Z., Li, X.-H., Zhang, L.-P., & Tung, C.-H. (2003). Versatile Photosensitization System for1O2-Mediated Oxidation of Alkenes Based on Nafion-Supported Platinum(II) Terpyridyl Acetylide Complex. Organic Letters, 5(18), 3221-3224. doi:10.1021/ol035012e

Gerdes, R., Bartels, O., Schneider, G., Wöhrle, D., & Schulz-Ekloff, G. (2001). Photooxidations of phenol, cyclopentadiene and citronellol with photosensitizers ionically bound at a polymeric ion exchanger. Polymers for Advanced Technologies, 12(3-4), 152-160. doi:10.1002/pat.126

Madhavan, D., & Pitchumani, K. (2001). Reactions in clay media: photooxidation of sulfides by clay-bound methylene blue. Tetrahedron, 57(39), 8391-8394. doi:10.1016/s0040-4020(01)00834-1

Soggiu, N., Cardy, H., Habib Jiwan, J. L., Leray, I., Soumillion, J. P., & Lacombe, S. (1999). Organic sulfides photooxidation using sensitizers covalently grafted on silica: towards a more efficient and selective solar photochemistry. Journal of Photochemistry and Photobiology A: Chemistry, 124(1-2), 1-8. doi:10.1016/s1010-6030(99)00060-x

Li, X., & Ramamurthy, V. (1996). Electron transfer reactions within zeolites: Photooxidation of stilbenes. Tetrahedron Letters, 37(30), 5235-5238. doi:10.1016/0040-4039(96)01073-8

Zhou, W., & Clennan, E. L. (1999). Organic Reactions in Zeolites. 1. Photooxidations of Sulfides in Methylene Blue Doped Zeolite Y. Journal of the American Chemical Society, 121(12), 2915-2916. doi:10.1021/ja984267y

Tanielian, C., Wolff, C., & Esch, M. (1996). Singlet Oxygen Production in Water:  Aggregation and Charge-Transfer Effects. The Journal of Physical Chemistry, 100(16), 6555-6560. doi:10.1021/jp952107s

Griesbeck, A. G., & Bartoschek, A. (2002). Sustainable photochemistry: solvent-free singlet oxygen-photooxygenation of organic substrates embedded in porphyrin-loaded polystyrene beadsDedicated to Professor Waldemar Adam on the occasion of his 65th birthday and his retirement from the stage of photooxygenation chemistry. Chemical Communications, (15), 1594-1595. doi:10.1039/b204017d

Griesbeck, A. G., El-Idreesy, T. T., & Lex, J. (2006). Singlet oxygen addition to chiral allylic alcohols and subsequent peroxyacetalization with β-naphthaldehyde: synthesis of diastereomerically pure 3-β-naphthyl-substituted 1,2,4-trioxanes. Tetrahedron, 62(46), 10615-10622. doi:10.1016/j.tet.2006.05.093

Kuroda, Y., Hiroshige, T., Sera, T., Shiroiwa, Y., Tanaka, H., & Ogoshi, H. (1989). Cyclodextrin-sandwiched porphyrin. Journal of the American Chemical Society, 111(5), 1912-1913. doi:10.1021/ja00187a073

Kuroda, Y., Sera, T., & Ogoshi, H. (1991). Regioselectivities and stereoselectivities of singlet oxygen generated by cyclodextrin-sandwiched porphyrin sensitization. Lipoxygenase-like activity. Journal of the American Chemical Society, 113(7), 2793-2794. doi:10.1021/ja00007a087

Joy, A., Robbins, R. J., Pitchumani, K., & Ramamurthy, V. (1997). Asymmetrically modified zeolite as a medium for enantioselective photoreactions: Reactions from spin forbidden excited states. Tetrahedron Letters, 38(51), 8825-8828. doi:10.1016/s0040-4039(97)10382-3

Sundén, H., Engqvist, M., Casas, J., Ibrahem, I., & Córdova, A. (2004). Direct Amino Acid Catalyzed Asymmetric α Oxidation of Ketones with Molecular Oxygen. Angewandte Chemie International Edition, 43(47), 6532-6535. doi:10.1002/anie.200460295

Córdova, A., Sundén, H., Engqvist, M., Ibrahem, I., & Casas, J. (2004). The Direct Amino Acid-Catalyzed Asymmetric Incorporation of Molecular Oxygen to Organic Compounds. Journal of the American Chemical Society, 126(29), 8914-8915. doi:10.1021/ja047930t

Griesbeck, A. G., Schäfer, M., & Uhlig, J. (2008). Photooxygenation Catalysis with a Polyol-Decorated Disc-Shaped Porphyrin Sensitizer: Shell-Recognition Effects. Advanced Synthesis & Catalysis, 350(13), 2104-2108. doi:10.1002/adsc.200800282

Maillard, P., Gaspard, S., Guerquin-Kern, J. L., & Momenteau, M. (1989). Glycoconjugated tetrapyrrolic macrocycles. Journal of the American Chemical Society, 111(25), 9125-9127. doi:10.1021/ja00207a033

Maillard, P., Guerquin-Kern, J. L., Huel, C., & Momenteau, M. (1993). Glycoconjugated porphyrins. 2. Synthesis of sterically constrained polyglycosylated compounds derived from tetraphenylporphyrins. The Journal of Organic Chemistry, 58(10), 2774-2780. doi:10.1021/jo00062a020

Kohata, K., Higashio, H., Yamaguchi, Y., Koketsu, M., & Odashima, T. (1994). Synthesis and Characterization of New Style of Water-Soluble Glycosylated Porphyrins as a Spectrophotometric Reagent for Metal Ions. Bulletin of the Chemical Society of Japan, 67(3), 668-679. doi:10.1246/bcsj.67.668

Naik, N., & Braslau, R. (1998). Synthesis and applications of optically active nitroxides. Tetrahedron, 54(5-6), 667-696. doi:10.1016/s0040-4020(97)10061-8

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