Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate

Autores
Bonaterra, Mariana; Rossi, Roberto Arturo; Martín, Sandra Elizabeth
Año de publicación
2009
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
We have studied the Pd-catalyzed cross-coupling reaction of organoheteroatom stannanes containing elements of groups 15 (P, As, Sb) and 16 (Se) with 1-naphthyl triflate (3). The stannanes n-Bu3SnZPh n (Z = P, As, Sb, Se; n = 1,2) were synthesized by the reaction of the PhnZ- anion with n-Bu3SnCl. The cross-coupling reactions of these stannanes with 3 in a one-pot procedure afforded the C - heteroatom products PhnZ-1-Naph in good yields for Z = As, Se (90 and 70% yields, respectively) and moderate yields for Z = P (51% yield). Only 18% of 1-naphthyldiphenylstibine was obtained. Optimization studies revealed that the combination of LiCl and free PPh3 ligand proved to be particularly effective in enhancing the coupling reaction.
Fil: Bonaterra, Mariana. 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: Rossi, Roberto Arturo. 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
Organoheteroatom Stannanes
Palladium
Triflates
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:11336/74040
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/74040
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflateBonaterra, MarianaRossi, Roberto ArturoMartín, Sandra ElizabethOrganoheteroatom StannanesPalladiumTriflatesCross-Couplinghttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1We have studied the Pd-catalyzed cross-coupling reaction of organoheteroatom stannanes containing elements of groups 15 (P, As, Sb) and 16 (Se) with 1-naphthyl triflate (3). The stannanes n-Bu3SnZPh n (Z = P, As, Sb, Se; n = 1,2) were synthesized by the reaction of the PhnZ- anion with n-Bu3SnCl. The cross-coupling reactions of these stannanes with 3 in a one-pot procedure afforded the C - heteroatom products PhnZ-1-Naph in good yields for Z = As, Se (90 and 70% yields, respectively) and moderate yields for Z = P (51% yield). Only 18% of 1-naphthyldiphenylstibine was obtained. Optimization studies revealed that the combination of LiCl and free PPh3 ligand proved to be particularly effective in enhancing the coupling reaction.Fil: Bonaterra, Mariana. 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: Rossi, Roberto Arturo. 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; ArgentinaAmerican Chemical Society2009-02info: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/11336/74040Bonaterra, Mariana; Rossi, Roberto Arturo; Martín, Sandra Elizabeth; Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate; American Chemical Society; Organometallics; 28; 3; 2-2009; 933-9360276-7333CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/om8009816info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/om8009816info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-29T12:03:42Zoai:ri.conicet.gov.ar:11336/74040instacron: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:34982025-10-29 12:03:42.932CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate
title Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate
spellingShingle Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate
Bonaterra, Mariana
Organoheteroatom Stannanes
Palladium
Triflates
Cross-Coupling
title_short Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate
title_full Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate
title_fullStr Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate
title_full_unstemmed Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate
title_sort Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate
dc.creator.none.fl_str_mv Bonaterra, Mariana
Rossi, Roberto Arturo
Martín, Sandra Elizabeth
author Bonaterra, Mariana
author_facet Bonaterra, Mariana
Rossi, Roberto Arturo
Martín, Sandra Elizabeth
author_role author
author2 Rossi, Roberto Arturo
Martín, Sandra Elizabeth
author2_role author
author
dc.subject.none.fl_str_mv Organoheteroatom Stannanes
Palladium
Triflates
Cross-Coupling
topic Organoheteroatom Stannanes
Palladium
Triflates
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 We have studied the Pd-catalyzed cross-coupling reaction of organoheteroatom stannanes containing elements of groups 15 (P, As, Sb) and 16 (Se) with 1-naphthyl triflate (3). The stannanes n-Bu3SnZPh n (Z = P, As, Sb, Se; n = 1,2) were synthesized by the reaction of the PhnZ- anion with n-Bu3SnCl. The cross-coupling reactions of these stannanes with 3 in a one-pot procedure afforded the C - heteroatom products PhnZ-1-Naph in good yields for Z = As, Se (90 and 70% yields, respectively) and moderate yields for Z = P (51% yield). Only 18% of 1-naphthyldiphenylstibine was obtained. Optimization studies revealed that the combination of LiCl and free PPh3 ligand proved to be particularly effective in enhancing the coupling reaction.
Fil: Bonaterra, Mariana. 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: Rossi, Roberto Arturo. 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 We have studied the Pd-catalyzed cross-coupling reaction of organoheteroatom stannanes containing elements of groups 15 (P, As, Sb) and 16 (Se) with 1-naphthyl triflate (3). The stannanes n-Bu3SnZPh n (Z = P, As, Sb, Se; n = 1,2) were synthesized by the reaction of the PhnZ- anion with n-Bu3SnCl. The cross-coupling reactions of these stannanes with 3 in a one-pot procedure afforded the C - heteroatom products PhnZ-1-Naph in good yields for Z = As, Se (90 and 70% yields, respectively) and moderate yields for Z = P (51% yield). Only 18% of 1-naphthyldiphenylstibine was obtained. Optimization studies revealed that the combination of LiCl and free PPh3 ligand proved to be particularly effective in enhancing the coupling reaction.
publishDate 2009
dc.date.none.fl_str_mv 2009-02
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/11336/74040
Bonaterra, Mariana; Rossi, Roberto Arturo; Martín, Sandra Elizabeth; Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate; American Chemical Society; Organometallics; 28; 3; 2-2009; 933-936
0276-7333
CONICET Digital
CONICET
url http://hdl.handle.net/11336/74040
identifier_str_mv Bonaterra, Mariana; Rossi, Roberto Arturo; Martín, Sandra Elizabeth; Organoheteroatom stannanes in palladium-catalyzed cross-coupling reactions with 1-naphthyl triflate; American Chemical Society; Organometallics; 28; 3; 2-2009; 933-936
0276-7333
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/om8009816
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/om8009816
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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 13.10058

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