Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions

Autores
Gerbino, Darío César; Mandolesi, Sandra Delia; Schmalz, Hans Günther; Podestá, Julio Cesar
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This paper reports some studies aiming at the developement of a general protocol useful for the synthesis of allyl- and prenylaromatic compounds. The first part deals with, the preparation of boron reagents like arylboronic acids and their pinacol esters as well as of pinacol allyl- and prenylboronates. The second part of the paper is devoted to the use of these boron reagents in Suzuki-Miyaura cross-coupling reactions leading to allylation and prenylation of aromatic compounds. Of the six methods studied, the most promising re-suits were obtained by using the Pd2(dba)3-catalyzed reactions of arylboronic acids with allyl and prenyl bromides, that lead to the products of cross coupling in high yields (average 87%), and the reactions of aryl trifluoroborates with allyl and prenyl bromides catalyzed by Pd(OAc)2 that lead to the products of coupling in all cases in high yields (average 82%). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
Fil: Gerbino, Darío César. 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; Argentina
Fil: Mandolesi, Sandra Delia. 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; Argentina
Fil: Schmalz, Hans Günther. Universität zu Köln; Alemania
Fil: 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; Argentina
Materia
Arenes
Borates
Boron
Cross-Coupling
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:11336/65714
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactionsGerbino, Darío CésarMandolesi, Sandra DeliaSchmalz, Hans GüntherPodestá, Julio CesarArenesBoratesBoronCross-Couplinghttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1This paper reports some studies aiming at the developement of a general protocol useful for the synthesis of allyl- and prenylaromatic compounds. The first part deals with, the preparation of boron reagents like arylboronic acids and their pinacol esters as well as of pinacol allyl- and prenylboronates. The second part of the paper is devoted to the use of these boron reagents in Suzuki-Miyaura cross-coupling reactions leading to allylation and prenylation of aromatic compounds. Of the six methods studied, the most promising re-suits were obtained by using the Pd2(dba)3-catalyzed reactions of arylboronic acids with allyl and prenyl bromides, that lead to the products of cross coupling in high yields (average 87%), and the reactions of aryl trifluoroborates with allyl and prenyl bromides catalyzed by Pd(OAc)2 that lead to the products of coupling in all cases in high yields (average 82%). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.Fil: Gerbino, Darío César. 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: Mandolesi, Sandra Delia. 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: Schmalz, Hans Günther. Universität zu Köln; AlemaniaFil: 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; ArgentinaWiley VCH Verlag2009-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/65714Gerbino, Darío César; Mandolesi, Sandra Delia; Schmalz, Hans Günther; Podestá, Julio Cesar; Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions; Wiley VCH Verlag; European Journal of Organic Chemistry; 23; 8-2009; 3964-39721434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.200900234info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200900234info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:47:06Zoai:ri.conicet.gov.ar:11336/65714instacron: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:34982025-09-03 09:47:06.856CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions
title Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions
spellingShingle Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions
Gerbino, Darío César
Arenes
Borates
Boron
Cross-Coupling
title_short Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions
title_full Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions
title_fullStr Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions
title_full_unstemmed Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions
title_sort Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions
dc.creator.none.fl_str_mv Gerbino, Darío César
Mandolesi, Sandra Delia
Schmalz, Hans Günther
Podestá, Julio Cesar
author Gerbino, Darío César
author_facet Gerbino, Darío César
Mandolesi, Sandra Delia
Schmalz, Hans Günther
Podestá, Julio Cesar
author_role author
author2 Mandolesi, Sandra Delia
Schmalz, Hans Günther
Podestá, Julio Cesar
author2_role author
author
author
dc.subject.none.fl_str_mv Arenes
Borates
Boron
Cross-Coupling
topic Arenes
Borates
Boron
Cross-Coupling
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv This paper reports some studies aiming at the developement of a general protocol useful for the synthesis of allyl- and prenylaromatic compounds. The first part deals with, the preparation of boron reagents like arylboronic acids and their pinacol esters as well as of pinacol allyl- and prenylboronates. The second part of the paper is devoted to the use of these boron reagents in Suzuki-Miyaura cross-coupling reactions leading to allylation and prenylation of aromatic compounds. Of the six methods studied, the most promising re-suits were obtained by using the Pd2(dba)3-catalyzed reactions of arylboronic acids with allyl and prenyl bromides, that lead to the products of cross coupling in high yields (average 87%), and the reactions of aryl trifluoroborates with allyl and prenyl bromides catalyzed by Pd(OAc)2 that lead to the products of coupling in all cases in high yields (average 82%). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
Fil: Gerbino, Darío César. 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; Argentina
Fil: Mandolesi, Sandra Delia. 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; Argentina
Fil: Schmalz, Hans Günther. Universität zu Köln; Alemania
Fil: 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; Argentina
description This paper reports some studies aiming at the developement of a general protocol useful for the synthesis of allyl- and prenylaromatic compounds. The first part deals with, the preparation of boron reagents like arylboronic acids and their pinacol esters as well as of pinacol allyl- and prenylboronates. The second part of the paper is devoted to the use of these boron reagents in Suzuki-Miyaura cross-coupling reactions leading to allylation and prenylation of aromatic compounds. Of the six methods studied, the most promising re-suits were obtained by using the Pd2(dba)3-catalyzed reactions of arylboronic acids with allyl and prenyl bromides, that lead to the products of cross coupling in high yields (average 87%), and the reactions of aryl trifluoroborates with allyl and prenyl bromides catalyzed by Pd(OAc)2 that lead to the products of coupling in all cases in high yields (average 82%). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
publishDate 2009
dc.date.none.fl_str_mv 2009-08
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/11336/65714
Gerbino, Darío César; Mandolesi, Sandra Delia; Schmalz, Hans Günther; Podestá, Julio Cesar; Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions; Wiley VCH Verlag; European Journal of Organic Chemistry; 23; 8-2009; 3964-3972
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/65714
identifier_str_mv Gerbino, Darío César; Mandolesi, Sandra Delia; Schmalz, Hans Günther; Podestá, Julio Cesar; Introduction of allyi and prenyl side-chains into aromatic systems by suzuki cross-coupling reactions; Wiley VCH Verlag; European Journal of Organic Chemistry; 23; 8-2009; 3964-3972
1434-193X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.200900234
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200900234
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
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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
_version_ 1842268837690474496
score 13.13397

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