Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction

Autores
Quinteros, Gisela Julieta; Uberman, Paula Marina; Martín, Sandra Elizabeth
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Biphenyl-based arsine ligands were prepared in two-step fashion by Pd-catalyzed arsination and microwave-assisted Suzuki-Miyaura coupling, providing sterically demanding arsine ligands in overall isolated yields up to 82 % as air-stable solids. Short reaction times were achieved with the assistance of microwave irradiation in the direct and simple described protocol for the synthesis of biarylarsine ligands. The activities of the biphenyl arsine ligands were explored in Pd-catalyzed Heck coupling. As a general trend, the ligands with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone performed more efficiently in the coupling reaction. This catalytic system allowed several interesting stilbenes to be obtained in very good yields. Sterically demanding biphenyl-based arsine ligands were prepared in high overall yields by microwave-assisted Suzuki-Miyaura coupling. The ligands were evaluated in the Pd-catalyzed Heck coupling reaction; the most active were those with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone.
Fil: Quinteros, Gisela Julieta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Uberman, Paula Marina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Martín, Sandra Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
As Ligands
Cross Coupling
Homogeneous Catalysis
Ligand Design
Microwave Chemistry
Palladium
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:11336/39673
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/39673
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reactionQuinteros, Gisela JulietaUberman, Paula MarinaMartín, Sandra ElizabethAs LigandsCross CouplingHomogeneous CatalysisLigand DesignMicrowave ChemistryPalladiumhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Biphenyl-based arsine ligands were prepared in two-step fashion by Pd-catalyzed arsination and microwave-assisted Suzuki-Miyaura coupling, providing sterically demanding arsine ligands in overall isolated yields up to 82 % as air-stable solids. Short reaction times were achieved with the assistance of microwave irradiation in the direct and simple described protocol for the synthesis of biarylarsine ligands. The activities of the biphenyl arsine ligands were explored in Pd-catalyzed Heck coupling. As a general trend, the ligands with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone performed more efficiently in the coupling reaction. This catalytic system allowed several interesting stilbenes to be obtained in very good yields. Sterically demanding biphenyl-based arsine ligands were prepared in high overall yields by microwave-assisted Suzuki-Miyaura coupling. The ligands were evaluated in the Pd-catalyzed Heck coupling reaction; the most active were those with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone.Fil: Quinteros, Gisela Julieta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Uberman, Paula Marina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Martín, Sandra Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaWiley VCH Verlag2015-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/39673Quinteros, Gisela Julieta; Uberman, Paula Marina; Martín, Sandra Elizabeth; Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction; Wiley VCH Verlag; European Journal of Organic Chemistry; 2015; 12; 4-2015; 2698-27051434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201403658info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201403658info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:30:58Zoai:ri.conicet.gov.ar:11336/39673instacron: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 10:30:58.567CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction
title Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction
spellingShingle Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction
Quinteros, Gisela Julieta
As Ligands
Cross Coupling
Homogeneous Catalysis
Ligand Design
Microwave Chemistry
Palladium
title_short Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction
title_full Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction
title_fullStr Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction
title_full_unstemmed Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction
title_sort Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction
dc.creator.none.fl_str_mv Quinteros, Gisela Julieta
Uberman, Paula Marina
Martín, Sandra Elizabeth
author Quinteros, Gisela Julieta
author_facet Quinteros, Gisela Julieta
Uberman, Paula Marina
Martín, Sandra Elizabeth
author_role author
author2 Uberman, Paula Marina
Martín, Sandra Elizabeth
author2_role author
author
dc.subject.none.fl_str_mv As Ligands
Cross Coupling
Homogeneous Catalysis
Ligand Design
Microwave Chemistry
Palladium
topic As Ligands
Cross Coupling
Homogeneous Catalysis
Ligand Design
Microwave Chemistry
Palladium
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Biphenyl-based arsine ligands were prepared in two-step fashion by Pd-catalyzed arsination and microwave-assisted Suzuki-Miyaura coupling, providing sterically demanding arsine ligands in overall isolated yields up to 82 % as air-stable solids. Short reaction times were achieved with the assistance of microwave irradiation in the direct and simple described protocol for the synthesis of biarylarsine ligands. The activities of the biphenyl arsine ligands were explored in Pd-catalyzed Heck coupling. As a general trend, the ligands with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone performed more efficiently in the coupling reaction. This catalytic system allowed several interesting stilbenes to be obtained in very good yields. Sterically demanding biphenyl-based arsine ligands were prepared in high overall yields by microwave-assisted Suzuki-Miyaura coupling. The ligands were evaluated in the Pd-catalyzed Heck coupling reaction; the most active were those with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone.
Fil: Quinteros, Gisela Julieta. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Uberman, Paula Marina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Martín, Sandra Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description Biphenyl-based arsine ligands were prepared in two-step fashion by Pd-catalyzed arsination and microwave-assisted Suzuki-Miyaura coupling, providing sterically demanding arsine ligands in overall isolated yields up to 82 % as air-stable solids. Short reaction times were achieved with the assistance of microwave irradiation in the direct and simple described protocol for the synthesis of biarylarsine ligands. The activities of the biphenyl arsine ligands were explored in Pd-catalyzed Heck coupling. As a general trend, the ligands with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone performed more efficiently in the coupling reaction. This catalytic system allowed several interesting stilbenes to be obtained in very good yields. Sterically demanding biphenyl-based arsine ligands were prepared in high overall yields by microwave-assisted Suzuki-Miyaura coupling. The ligands were evaluated in the Pd-catalyzed Heck coupling reaction; the most active were those with "blocked" ortho-positions on the non-arsine-containing ring of the biphenyl backbone.
publishDate 2015
dc.date.none.fl_str_mv 2015-04
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/11336/39673
Quinteros, Gisela Julieta; Uberman, Paula Marina; Martín, Sandra Elizabeth; Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction; Wiley VCH Verlag; European Journal of Organic Chemistry; 2015; 12; 4-2015; 2698-2705
1434-193X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/39673
identifier_str_mv Quinteros, Gisela Julieta; Uberman, Paula Marina; Martín, Sandra Elizabeth; Bulky monodentate biphenylarsine ligands: Synthesis and evaluation of their structure effects in the palladium-catalyzed Heck reaction; Wiley VCH Verlag; European Journal of Organic Chemistry; 2015; 12; 4-2015; 2698-2705
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.201403658
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201403658
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 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
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score 13.070432

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