Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts

In this work, some results of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone are presented. The employed catalysts were platinum-based modified with organotin precursors either chiral (Men3Sn-SnMen3) or achiral (SnBu4), and they were obtained via surface...

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Autores: Vetere, Virginia, Faraoni, María Belén, Santori, Gerardo Fabian, Podestá, Julio Cesar, Casella, Mónica Laura, Ferretti, Osmar Alberto
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2005
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/56075
Acceso en línea:http://hdl.handle.net/11336/56075
Access Level:acceso abierto
Palabra clave:3,4-Dimethoxyacetophenone
Acetophenone
Enantioselectivity
Hydrogenation
Men3sn-Snmen3
Organometallic Catalysts
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
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oai_identifier_str oai:ri.conicet.gov.ar:11336/56075
network_acronym_str AR
network_name_str Argentina
repository_id_str
dc.title.none.fl_str_mv Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts
title Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts
spellingShingle Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts
Vetere, Virginia
3,4-Dimethoxyacetophenone
Acetophenone
Enantioselectivity
Hydrogenation
Men3sn-Snmen3
Organometallic Catalysts
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
title_short Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts
title_full Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts
title_fullStr Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts
title_full_unstemmed Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts
title_sort Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts
dc.creator.none.fl_str_mv Vetere, Virginia
Faraoni, María Belén
Santori, Gerardo Fabian
Podestá, Julio Cesar
Casella, Mónica Laura
Ferretti, Osmar Alberto
author Vetere, Virginia
author_facet Vetere, Virginia
Faraoni, María Belén
Santori, Gerardo Fabian
Podestá, Julio Cesar
Casella, Mónica Laura
Ferretti, Osmar Alberto
author_role author
author2 Faraoni, María Belén
Santori, Gerardo Fabian
Podestá, Julio Cesar
Casella, Mónica Laura
Ferretti, Osmar Alberto
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv 3,4-Dimethoxyacetophenone
Acetophenone
Enantioselectivity
Hydrogenation
Men3sn-Snmen3
Organometallic Catalysts
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
topic 3,4-Dimethoxyacetophenone
Acetophenone
Enantioselectivity
Hydrogenation
Men3sn-Snmen3
Organometallic Catalysts
https://purl.org/becyt/ford/2.4
https://purl.org/becyt/ford/2
description In this work, some results of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone are presented. The employed catalysts were platinum-based modified with organotin precursors either chiral (Men3Sn-SnMen3) or achiral (SnBu4), and they were obtained via surface organometallic chemistry on metals (SOMC/M) techniques. The presence of organotin fragments on the catalyst surface inhibits the aromatic ring hydrogenation, leading to the hydrogenation of both acetophenone and 3,4-dimethoxyacetophenone to the corresponding alcohol with selectivity higher than 99%. With both substrates, a rate acceleration when changing from the achiral catalyst PtSn-OM to the chiral one, PtSn-OM* was observed. The presence of menthyl groups may be responsible for the rate acceleration in the key step of enantiodifferentiation. In the 3,4-dimethoxyacetophenone hydrogenation, 39% enantiomeric excess was obtained, with a selectivity of nearly 100%.
publishDate 2005
dc.date.none.fl_str_mv 2005-10
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/56075
Vetere, Virginia; Faraoni, María Belén; Santori, Gerardo Fabian; Podestá, Julio Cesar; Casella, Mónica Laura; et al.; Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts; Elsevier Science; Catalysis Today; 107-108; 10-2005; 266-272
0920-5861
CONICET Digital
CONICET
url http://hdl.handle.net/11336/56075
identifier_str_mv Vetere, Virginia; Faraoni, María Belén; Santori, Gerardo Fabian; Podestá, Julio Cesar; Casella, Mónica Laura; et al.; Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts; Elsevier Science; Catalysis Today; 107-108; 10-2005; 266-272
0920-5861
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.cattod.2005.07.079
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0920586105003664
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1799196083476234240
spelling Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalystsVetere, VirginiaFaraoni, María BelénSantori, Gerardo FabianPodestá, Julio CesarCasella, Mónica LauraFerretti, Osmar Alberto3,4-DimethoxyacetophenoneAcetophenoneEnantioselectivityHydrogenationMen3sn-Snmen3Organometallic Catalystshttps://purl.org/becyt/ford/2.4https://purl.org/becyt/ford/2In this work, some results of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone are presented. The employed catalysts were platinum-based modified with organotin precursors either chiral (Men3Sn-SnMen3) or achiral (SnBu4), and they were obtained via surface organometallic chemistry on metals (SOMC/M) techniques. The presence of organotin fragments on the catalyst surface inhibits the aromatic ring hydrogenation, leading to the hydrogenation of both acetophenone and 3,4-dimethoxyacetophenone to the corresponding alcohol with selectivity higher than 99%. With both substrates, a rate acceleration when changing from the achiral catalyst PtSn-OM to the chiral one, PtSn-OM* was observed. The presence of menthyl groups may be responsible for the rate acceleration in the key step of enantiodifferentiation. In the 3,4-dimethoxyacetophenone hydrogenation, 39% enantiomeric excess was obtained, with a selectivity of nearly 100%.Fil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Faraoni, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Santori, Gerardo Fabian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Podestá, Julio Cesar. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Casella, Mónica Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Ferretti, Osmar Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaElsevier Science2005-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/56075Vetere, Virginia; Faraoni, María Belén; Santori, Gerardo Fabian; Podestá, Julio Cesar; Casella, Mónica Laura; et al.; Study of the racemic and enantioselective hydrogenation of acetophenone and 3,4-dimethoxyacetophenone using platinum-based organotin catalysts; Elsevier Science; Catalysis Today; 107-108; 10-2005; 266-2720920-5861CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.cattod.2005.07.079info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0920586105003664info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T14:14:05Zoai:ri.conicet.gov.ar:11336/56075instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982024-05-08 14:14:05.427CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
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