Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols

Autores
Chopa, Alicia Beatriz; Silbestri, Gustavo Fabián; Lockhart, María Teresa
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A series of arylstannanes have been synthesized, through an SRN1 mechanism, in good to excellent yields (74%-99%) by the photostimulated reaction of trimethyl stannyl ion with substrates supporting different nucleofugal groups. The arylstannanes thus obtained were suitable intermediates for Stille cross-coupling reactions leading to asymmetric bi- and triaryl compounds in acceptable global yields. An attractive feature of this route is that simple commercially available benzenediols, chloro- and methoxy phenols might be useful starting substrates, leading the latter to higher global yields of products in fewer steps. The strategies proposed open a broad synthetic tool.
Fil: Chopa, Alicia Beatriz. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina
Fil: Silbestri, Gustavo Fabián. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina
Fil: Lockhart, María Teresa. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina
Materia
ARYLSTANNANES
BIPHENYLS
SRN1
STILLE REACTION
TERPHENYLS
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:11336/97566
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenolsChopa, Alicia BeatrizSilbestri, Gustavo FabiánLockhart, María TeresaARYLSTANNANESBIPHENYLSSRN1STILLE REACTIONTERPHENYLShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A series of arylstannanes have been synthesized, through an SRN1 mechanism, in good to excellent yields (74%-99%) by the photostimulated reaction of trimethyl stannyl ion with substrates supporting different nucleofugal groups. The arylstannanes thus obtained were suitable intermediates for Stille cross-coupling reactions leading to asymmetric bi- and triaryl compounds in acceptable global yields. An attractive feature of this route is that simple commercially available benzenediols, chloro- and methoxy phenols might be useful starting substrates, leading the latter to higher global yields of products in fewer steps. The strategies proposed open a broad synthetic tool.Fil: Chopa, Alicia Beatriz. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; ArgentinaFil: Silbestri, Gustavo Fabián. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; ArgentinaFil: Lockhart, María Teresa. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; ArgentinaElsevier Science Sa2005-09-01info: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/11336/97566Chopa, Alicia Beatriz; Silbestri, Gustavo Fabián; Lockhart, María Teresa; Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols; Elsevier Science Sa; Journal of Organometallic Chemistry; 690; 17; 1-9-2005; 3865-38770022-328XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0022328X05004018info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jorganchem.2005.05.023info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:44:13Zoai:ri.conicet.gov.ar:11336/97566instacron: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 09:44:13.99CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols
title Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols
spellingShingle Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols
Chopa, Alicia Beatriz
ARYLSTANNANES
BIPHENYLS
SRN1
STILLE REACTION
TERPHENYLS
title_short Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols
title_full Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols
title_fullStr Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols
title_full_unstemmed Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols
title_sort Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols
dc.creator.none.fl_str_mv Chopa, Alicia Beatriz
Silbestri, Gustavo Fabián
Lockhart, María Teresa
author Chopa, Alicia Beatriz
author_facet Chopa, Alicia Beatriz
Silbestri, Gustavo Fabián
Lockhart, María Teresa
author_role author
author2 Silbestri, Gustavo Fabián
Lockhart, María Teresa
author2_role author
author
dc.subject.none.fl_str_mv ARYLSTANNANES
BIPHENYLS
SRN1
STILLE REACTION
TERPHENYLS
topic ARYLSTANNANES
BIPHENYLS
SRN1
STILLE REACTION
TERPHENYLS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A series of arylstannanes have been synthesized, through an SRN1 mechanism, in good to excellent yields (74%-99%) by the photostimulated reaction of trimethyl stannyl ion with substrates supporting different nucleofugal groups. The arylstannanes thus obtained were suitable intermediates for Stille cross-coupling reactions leading to asymmetric bi- and triaryl compounds in acceptable global yields. An attractive feature of this route is that simple commercially available benzenediols, chloro- and methoxy phenols might be useful starting substrates, leading the latter to higher global yields of products in fewer steps. The strategies proposed open a broad synthetic tool.
Fil: Chopa, Alicia Beatriz. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina
Fil: Silbestri, Gustavo Fabián. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca; Argentina
Fil: Lockhart, María Teresa. Universidad Nacional del Sur. Departamento de Química. Instituto de Investigaciones en Química Orgánica; Argentina
description A series of arylstannanes have been synthesized, through an SRN1 mechanism, in good to excellent yields (74%-99%) by the photostimulated reaction of trimethyl stannyl ion with substrates supporting different nucleofugal groups. The arylstannanes thus obtained were suitable intermediates for Stille cross-coupling reactions leading to asymmetric bi- and triaryl compounds in acceptable global yields. An attractive feature of this route is that simple commercially available benzenediols, chloro- and methoxy phenols might be useful starting substrates, leading the latter to higher global yields of products in fewer steps. The strategies proposed open a broad synthetic tool.
publishDate 2005
dc.date.none.fl_str_mv 2005-09-01
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/11336/97566
Chopa, Alicia Beatriz; Silbestri, Gustavo Fabián; Lockhart, María Teresa; Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols; Elsevier Science Sa; Journal of Organometallic Chemistry; 690; 17; 1-9-2005; 3865-3877
0022-328X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/97566
identifier_str_mv Chopa, Alicia Beatriz; Silbestri, Gustavo Fabián; Lockhart, María Teresa; Strategies for the synthesis of bi- and triarylic materials starting from commercially available phenols; Elsevier Science Sa; Journal of Organometallic Chemistry; 690; 17; 1-9-2005; 3865-3877
0022-328X
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://www.sciencedirect.com/science/article/pii/S0022328X05004018
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jorganchem.2005.05.023
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 Elsevier Science Sa
publisher.none.fl_str_mv Elsevier Science Sa
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 13.13397

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