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Beyond Acid Strength in Zeolites: Soft Framework Counteranions for Stabilization of Carbocations on Zeolites and Its Implication in Organic Synthesis

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Beyond Acid Strength in Zeolites: Soft Framework Counteranions for Stabilization of Carbocations on Zeolites and Its Implication in Organic Synthesis

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dc.contributor.author Cabrero Antonino, Jose Ramón es_ES
dc.contributor.author Leyva Perez, Antonio es_ES
dc.contributor.author Corma Canós, Avelino es_ES
dc.date.accessioned 2016-06-09T13:15:20Z
dc.date.available 2016-06-09T13:15:20Z
dc.date.issued 2015-05-04
dc.identifier.issn 1433-7851
dc.identifier.uri http://hdl.handle.net/10251/65606
dc.description.abstract [EN] The generation of a carbocation with an acid depends not only on the acid strength but also on the ability of the counteranion to stabilize the positive charge left behind. Here we report that despite their relatively weak acidity, zeolites are able to generate and stabilize medium-size (molecular weight approximate to 300 Da) delocalized carbocations on their surface under mild reaction conditions, as it can be done by strong Bronsted or Lewis acids in solution. The zeolite thus acts as a soft macroanion, prolonging the lifetime of the carbocation sufficiently to perform multifunctionalization reactions with amides, thioamides, and phenols, with high yield and selectivity. Biological studies show that some of the products obtained here present significant inhibition activity against colon cancer cells, illustrating the new possibilities of zeolites to prepare complex organic molecules. es_ES
dc.description.sponsorship This work was supported by Consolider-Ingenio 2010 (proyecto MULTICAT) and Severo Ochoa program. J.R.C.-A. and A. L.-P. thank ITQ for a fellowship. We thank Dr. S. Valencia for providing H-Beta nanocrystalline zeolite and Dr. U. Diaz for providing ITQ-2 zeolite. OIDD screening data supplied by courtesy of Eli Lilly and Company-used with Lilly's permission. en_EN
dc.language Inglés es_ES
dc.publisher Wiley es_ES
dc.relation Consolider-Ingenio 2010 (proyecto MULTICAT) es_ES
dc.relation Severo Ochoa program es_ES
dc.relation ITQ es_ES
dc.relation.ispartof Angewandte Chemie International Edition es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Carbocations es_ES
dc.subject Cycloaddition reactions es_ES
dc.subject Heterogeneous catalysis es_ES
dc.subject Propargyl alcohols es_ES
dc.subject zeolites es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.title Beyond Acid Strength in Zeolites: Soft Framework Counteranions for Stabilization of Carbocations on Zeolites and Its Implication in Organic Synthesis es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1002/anie.201500864
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 Cabrero Antonino, JR.; Leyva Perez, A.; Corma Canós, A. (2015). Beyond Acid Strength in Zeolites: Soft Framework Counteranions for Stabilization of Carbocations on Zeolites and Its Implication in Organic Synthesis. Angewandte Chemie International Edition. 54(19):5658-5661. doi:10.1002/anie.201500864 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://dx.doi.org/10.1002/anie.201500864 es_ES
dc.description.upvformatpinicio 5658 es_ES
dc.description.upvformatpfin 5661 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 54 es_ES
dc.description.issue 19 es_ES
dc.relation.senia 309547 es_ES
dc.identifier.eissn 1521-3773


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