A facile microwave-assisted Diels-Alder reaction of vinylboronates

Autores
Sarotti, Ariel Marcelo; Pisano, Pablo Luis; Pellegrinet, Silvina Carla
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The Diels-Alder reaction of vinylboronates can be easily performed using microwave irradiation giving excellent yields of the cycloadducts. Pinacol vinylboronate was the reagent of choice due to its stability towards hydrolysis, operational simplicity and yields of Diels-Alder products. To the best of our knowledge, this is the first example of microwave-assisted Diels-Alder reaction of boron-substituted dienophiles. Subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide afforded the alcohols efficiently.
Fil: Sarotti, Ariel Marcelo. 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: Pisano, Pablo Luis. 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: Pellegrinet, Silvina Carla. 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
DIELS-ALDER
BORONIC ACID DERIVATIVE
MICROWAVE IRRADIATION
BORON COMPOUNDS
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:11336/127800
Acceder
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network_name_str CONICET Digital (CONICET)
spelling A facile microwave-assisted Diels-Alder reaction of vinylboronatesSarotti, Ariel MarceloPisano, Pablo LuisPellegrinet, Silvina CarlaDIELS-ALDERBORONIC ACID DERIVATIVEMICROWAVE IRRADIATIONBORON COMPOUNDShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The Diels-Alder reaction of vinylboronates can be easily performed using microwave irradiation giving excellent yields of the cycloadducts. Pinacol vinylboronate was the reagent of choice due to its stability towards hydrolysis, operational simplicity and yields of Diels-Alder products. To the best of our knowledge, this is the first example of microwave-assisted Diels-Alder reaction of boron-substituted dienophiles. Subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide afforded the alcohols efficiently.Fil: Sarotti, Ariel Marcelo. 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: Pisano, Pablo Luis. 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: Pellegrinet, Silvina Carla. 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; ArgentinaRoyal Society of Chemistry2010-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/127800Sarotti, Ariel Marcelo; Pisano, Pablo Luis; Pellegrinet, Silvina Carla; A facile microwave-assisted Diels-Alder reaction of vinylboronates; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 8; 22; 11-2010; 5069-50731477-0520CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2010/ob/c0ob00020e#!divAbstractinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C0OB00020Einfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:33:19Zoai:ri.conicet.gov.ar:11336/127800instacron: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 10:33:19.771CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A facile microwave-assisted Diels-Alder reaction of vinylboronates
title A facile microwave-assisted Diels-Alder reaction of vinylboronates
spellingShingle A facile microwave-assisted Diels-Alder reaction of vinylboronates
Sarotti, Ariel Marcelo
DIELS-ALDER
BORONIC ACID DERIVATIVE
MICROWAVE IRRADIATION
BORON COMPOUNDS
title_short A facile microwave-assisted Diels-Alder reaction of vinylboronates
title_full A facile microwave-assisted Diels-Alder reaction of vinylboronates
title_fullStr A facile microwave-assisted Diels-Alder reaction of vinylboronates
title_full_unstemmed A facile microwave-assisted Diels-Alder reaction of vinylboronates
title_sort A facile microwave-assisted Diels-Alder reaction of vinylboronates
dc.creator.none.fl_str_mv Sarotti, Ariel Marcelo
Pisano, Pablo Luis
Pellegrinet, Silvina Carla
author Sarotti, Ariel Marcelo
author_facet Sarotti, Ariel Marcelo
Pisano, Pablo Luis
Pellegrinet, Silvina Carla
author_role author
author2 Pisano, Pablo Luis
Pellegrinet, Silvina Carla
author2_role author
author
dc.subject.none.fl_str_mv DIELS-ALDER
BORONIC ACID DERIVATIVE
MICROWAVE IRRADIATION
BORON COMPOUNDS
topic DIELS-ALDER
BORONIC ACID DERIVATIVE
MICROWAVE IRRADIATION
BORON COMPOUNDS
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 Diels-Alder reaction of vinylboronates can be easily performed using microwave irradiation giving excellent yields of the cycloadducts. Pinacol vinylboronate was the reagent of choice due to its stability towards hydrolysis, operational simplicity and yields of Diels-Alder products. To the best of our knowledge, this is the first example of microwave-assisted Diels-Alder reaction of boron-substituted dienophiles. Subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide afforded the alcohols efficiently.
Fil: Sarotti, Ariel Marcelo. 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: Pisano, Pablo Luis. 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: Pellegrinet, Silvina Carla. 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 Diels-Alder reaction of vinylboronates can be easily performed using microwave irradiation giving excellent yields of the cycloadducts. Pinacol vinylboronate was the reagent of choice due to its stability towards hydrolysis, operational simplicity and yields of Diels-Alder products. To the best of our knowledge, this is the first example of microwave-assisted Diels-Alder reaction of boron-substituted dienophiles. Subsequent in situ oxidation of the cycloadducts with alkaline hydrogen peroxide afforded the alcohols efficiently.
publishDate 2010
dc.date.none.fl_str_mv 2010-11
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/11336/127800
Sarotti, Ariel Marcelo; Pisano, Pablo Luis; Pellegrinet, Silvina Carla; A facile microwave-assisted Diels-Alder reaction of vinylboronates; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 8; 22; 11-2010; 5069-5073
1477-0520
CONICET Digital
CONICET
url http://hdl.handle.net/11336/127800
identifier_str_mv Sarotti, Ariel Marcelo; Pisano, Pablo Luis; Pellegrinet, Silvina Carla; A facile microwave-assisted Diels-Alder reaction of vinylboronates; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 8; 22; 11-2010; 5069-5073
1477-0520
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/content/articlelanding/2010/ob/c0ob00020e#!divAbstract
info:eu-repo/semantics/altIdentifier/doi/10.1039/C0OB00020E
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
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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 13.069144

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