α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights

We have found that α-hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene. When stoichiometric quantities are used, excellent yields are obtained, while catalytic activities are moderate. DFT calculations suggested that the activation of the dienophile occur...

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Detalles Bibliográficos
Autores: Grimblat, Nicolas, Sarotti, Ariel Marcelo, Pisano, Pablo Luis, Pellegrinet, Silvina Carla
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2016
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/52487
Acceso en línea:http://hdl.handle.net/11336/52487
Access Level:acceso abierto
Palabra clave:DIELSALDER
A-HYDROXYACIDS
ORGANOBORANES
RATIONAL DESIGN
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
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repository_id_str
spelling α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insightsGrimblat, NicolasSarotti, Ariel MarceloPisano, Pablo LuisPellegrinet, Silvina CarlaDIELSALDERA-HYDROXYACIDSORGANOBORANESRATIONAL DESIGNhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We have found that α-hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene. When stoichiometric quantities are used, excellent yields are obtained, while catalytic activities are moderate. DFT calculations suggested that the activation of the dienophile occurs by ligand exchange with both functionalities of the α-hydroxyacid.Fil: Grimblat, Nicolas. 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: 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 Chemistry2016-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/52487Grimblat, Nicolas; Sarotti, Ariel Marcelo; Pisano, Pablo Luis; Pellegrinet, Silvina Carla; α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights; Royal Society of Chemistry; New Journal of Chemistry; 40; 3; 1-2016; 1966-19691144-0546CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c5nj03015cinfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2016/NJ/C5NJ03015Cinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:52:28Zoai:ri.conicet.gov.ar:11336/52487instacron: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 13:52:28.325CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights
title α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights
spellingShingle α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights
Grimblat, Nicolas
DIELSALDER
A-HYDROXYACIDS
ORGANOBORANES
RATIONAL DESIGN
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights
title_full α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights
title_fullStr α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights
title_full_unstemmed α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights
title_sort α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights
dc.creator.none.fl_str_mv Grimblat, Nicolas
Sarotti, Ariel Marcelo
Pisano, Pablo Luis
Pellegrinet, Silvina Carla
author Grimblat, Nicolas
author_facet Grimblat, Nicolas
Sarotti, Ariel Marcelo
Pisano, Pablo Luis
Pellegrinet, Silvina Carla
author_role author
author2 Sarotti, Ariel Marcelo
Pisano, Pablo Luis
Pellegrinet, Silvina Carla
author2_role author
author
author
dc.subject.none.fl_str_mv DIELSALDER
A-HYDROXYACIDS
ORGANOBORANES
RATIONAL DESIGN
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic DIELSALDER
A-HYDROXYACIDS
ORGANOBORANES
RATIONAL DESIGN
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description We have found that α-hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene. When stoichiometric quantities are used, excellent yields are obtained, while catalytic activities are moderate. DFT calculations suggested that the activation of the dienophile occurs by ligand exchange with both functionalities of the α-hydroxyacid.
publishDate 2016
dc.date.none.fl_str_mv 2016-01
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/11336/52487
Grimblat, Nicolas; Sarotti, Ariel Marcelo; Pisano, Pablo Luis; Pellegrinet, Silvina Carla; α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights; Royal Society of Chemistry; New Journal of Chemistry; 40; 3; 1-2016; 1966-1969
1144-0546
CONICET Digital
CONICET
url http://hdl.handle.net/11336/52487
identifier_str_mv Grimblat, Nicolas; Sarotti, Ariel Marcelo; Pisano, Pablo Luis; Pellegrinet, Silvina Carla; α-Hydroxyacids accelerate the Diels-Alder reaction of dibutyl vinylboronate with cyclopentadiene: Experimental results and mechanistic insights; Royal Society of Chemistry; New Journal of Chemistry; 40; 3; 1-2016; 1966-1969
1144-0546
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c5nj03015c
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2016/NJ/C5NJ03015C
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
application/pdf
application/pdf
application/pdf
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
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
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score 15,812429

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