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Regioselective Hydration of Alkynes by Iron(III) Lewis/Brønsted Catalysis

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Regioselective Hydration of Alkynes by Iron(III) Lewis/Brønsted Catalysis

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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 2013-11-15T11:56:25Z
dc.date.issued 2012-08-27
dc.identifier.issn 0947-6539
dc.identifier.uri http://hdl.handle.net/10251/33630
dc.description.abstract The triflimide iron(III) salt [Fe(NTf2)3] promotes the direct hydration of terminal and internal alkynes with very good Markovnikov regioselectivities and high yields. The enhanced carbophilic Lewis acidity of the FeIII cation mediated by the weakly-coordinating triflimide anion is crucial for the catalytic activity. The iron(III) metal salt can be recycled in the form of the OPPh3/[Fe(NTf2)3] system with similar activity and selectivity. However, spectroscopic and kinetic studies show that [Fe(NTf2)3] hydrolyzes under the reaction conditions and that catalytically less active Brønsted species are formed, which points to a Lewis/Brønsted co-catalysis. This triflimide-based catalytic system is regioselective for the hydration of internal aryl-alkynes and opens the door to a new synthetic route to alkyl ketophenones. As a proof of concept, the synthesis of two antipsychotics Haloperidol and Melperone, with general butyrophenone-like structure, is shown. es_ES
dc.description.sponsorship The work has been supported by Consolider-Ingenio 2010 (proyecto MULTICAT), and PROMETEO from Generalitat Valenciana. J.R.C.A. thanks MCIINN for a pre-doctoral FPU fellowship. A. L. P. thanks ITQ for financial support. We thank Dr. J. A. Vidal-Moya for the EPR measurements. en_EN
dc.format.extent 8 es_ES
dc.language Inglés es_ES
dc.publisher Wiley-VCH Verlag es_ES
dc.relation Consolider-Ingenio (proyecto MULTICAT) from Generalitat Valenciana es_ES
dc.relation PROMETEO from Generalitat Valenciana es_ES
dc.relation MCIINN es_ES
dc.relation ITQ es_ES
dc.relation.ispartof Chemistry - A European Journal es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Alkynes es_ES
dc.subject Anions es_ES
dc.subject Ketones es_ES
dc.subject Regioselectivity es_ES
dc.subject Iron es_ES
dc.subject Hydration es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Regioselective Hydration of Alkynes by Iron(III) Lewis/Brønsted Catalysis es_ES
dc.type Artículo es_ES
dc.embargo.lift 10000-01-01
dc.embargo.terms forever es_ES
dc.identifier.doi 10.1002/chem.201200580
dc.rights.accessRights Cerrado es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.description.bibliographicCitation Cabrero Antonino, JR.; Leyva Perez, A.; Corma Canós, A. (2012). Regioselective Hydration of Alkynes by Iron(III) Lewis/Brønsted Catalysis. Chemistry - A European Journal. 18(35):11107-11114. doi:10.1002/chem.201200580 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1002/chem.201200580 es_ES
dc.description.upvformatpinicio 11107 es_ES
dc.description.upvformatpfin 11114 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 18 es_ES
dc.description.issue 35 es_ES
dc.relation.senia 239329
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