Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome

Autores
la Venia, Agustina; Mischne, Mirta Paulina; Mata, Ernesto Gabino
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The gold-catalyzed intermolecular hydroalkylation of olefins with β-ketoesters represents a conceptually attractive and useful synthetic tool; however, it has been scarcely applied, remaining a challenge for chemists. The aim of the current study was to investigate the addition of these 1,3-diketo-compounds to alkenes under gold catalysis conditions, in order to establish the electronic and steric effects of the alkenyl substrates in the reaction outcome. The screening of different catalyst systems and diverse olefins enabled defining the alkenyl requirements and the best reaction conditions to efficiently achieve the coupled products.
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Mischne, Mirta Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Mata, Ernesto Gabino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
GOLD CATALYSIS
HYDROALKYLATION
OLEFINS
Β-KETOESTERS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/87172
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcomela Venia, AgustinaMischne, Mirta PaulinaMata, Ernesto GabinoGOLD CATALYSISHYDROALKYLATIONOLEFINSΒ-KETOESTERShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The gold-catalyzed intermolecular hydroalkylation of olefins with β-ketoesters represents a conceptually attractive and useful synthetic tool; however, it has been scarcely applied, remaining a challenge for chemists. The aim of the current study was to investigate the addition of these 1,3-diketo-compounds to alkenes under gold catalysis conditions, in order to establish the electronic and steric effects of the alkenyl substrates in the reaction outcome. The screening of different catalyst systems and diverse olefins enabled defining the alkenyl requirements and the best reaction conditions to efficiently achieve the coupled products.Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Mischne, Mirta Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Mata, Ernesto Gabino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaMolecular Diversity Preservation International2018-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/87172la Venia, Agustina; Mischne, Mirta Paulina; Mata, Ernesto Gabino; Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome; Molecular Diversity Preservation International; Molecules; 23; 3; 3-2018; 629-6401420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.mdpi.com/1420-3049/23/3/629info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules23030629info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:39:29Zoai:ri.conicet.gov.ar:11336/87172instacron: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:34982025-09-29 09:39:29.59CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome
title Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome
spellingShingle Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome
la Venia, Agustina
GOLD CATALYSIS
HYDROALKYLATION
OLEFINS
Β-KETOESTERS
title_short Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome
title_full Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome
title_fullStr Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome
title_full_unstemmed Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome
title_sort Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome
dc.creator.none.fl_str_mv la Venia, Agustina
Mischne, Mirta Paulina
Mata, Ernesto Gabino
author la Venia, Agustina
author_facet la Venia, Agustina
Mischne, Mirta Paulina
Mata, Ernesto Gabino
author_role author
author2 Mischne, Mirta Paulina
Mata, Ernesto Gabino
author2_role author
author
dc.subject.none.fl_str_mv GOLD CATALYSIS
HYDROALKYLATION
OLEFINS
Β-KETOESTERS
topic GOLD CATALYSIS
HYDROALKYLATION
OLEFINS
Β-KETOESTERS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The gold-catalyzed intermolecular hydroalkylation of olefins with β-ketoesters represents a conceptually attractive and useful synthetic tool; however, it has been scarcely applied, remaining a challenge for chemists. The aim of the current study was to investigate the addition of these 1,3-diketo-compounds to alkenes under gold catalysis conditions, in order to establish the electronic and steric effects of the alkenyl substrates in the reaction outcome. The screening of different catalyst systems and diverse olefins enabled defining the alkenyl requirements and the best reaction conditions to efficiently achieve the coupled products.
Fil: la Venia, Agustina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Mischne, Mirta Paulina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Mata, Ernesto Gabino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description The gold-catalyzed intermolecular hydroalkylation of olefins with β-ketoesters represents a conceptually attractive and useful synthetic tool; however, it has been scarcely applied, remaining a challenge for chemists. The aim of the current study was to investigate the addition of these 1,3-diketo-compounds to alkenes under gold catalysis conditions, in order to establish the electronic and steric effects of the alkenyl substrates in the reaction outcome. The screening of different catalyst systems and diverse olefins enabled defining the alkenyl requirements and the best reaction conditions to efficiently achieve the coupled products.
publishDate 2018
dc.date.none.fl_str_mv 2018-03
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/11336/87172
la Venia, Agustina; Mischne, Mirta Paulina; Mata, Ernesto Gabino; Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome; Molecular Diversity Preservation International; Molecules; 23; 3; 3-2018; 629-640
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/87172
identifier_str_mv la Venia, Agustina; Mischne, Mirta Paulina; Mata, Ernesto Gabino; Gold-catalyzed addition of β-ketoesters to alkenes: Influence of electronic and steric effects in the reaction outcome; Molecular Diversity Preservation International; Molecules; 23; 3; 3-2018; 629-640
1420-3049
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.mdpi.com/1420-3049/23/3/629
info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules23030629
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
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
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score 13.070432

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