Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination

Autores
Uberman, Paula Marina; Lanteri, Mario Nicolas; Parajón Puenzo, Sol Carolina; Martín, Sandra Elizabeth
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A versatile and efficient approach for the synthesis of new biphenyl-based arsine ligands, by a Pd-catalyzed arsination to introduce the -AsPh2 moiety, and then a Suzuki-Miyaura cross-coupling for biaryl construction is reported. By Pd-catalyzed arsination with n-Bu3SnAsPh2 (1), (2-bromophenyl)diphenylarsine (2, 83%) was obtained. The Suzuki-Miyaura reaction between the bromoarsine 2 and aryl boronic acids bearing different substituents provided biarylarsine ligands (80-99%). The efficiency of catalysts derived from the new biarylarsine ligands was evaluated in the Pd-catalyzed arsination with perfluoroalkyl iodides (RfI). Outstanding activities of catalysts derived from Pd/methoxybiarylarsine ligands were found in this coupling reaction affording perfluoroalkyl arsines in very good yields (57-100%). © 2011 The Royal Society of Chemistry.
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: Lanteri, Mario Nicolas. 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: Parajón Puenzo, Sol Carolina. 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
Arsine
Biphenyl
Palladium
Ligands
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:11336/62006
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/62006
network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsinationUberman, Paula MarinaLanteri, Mario NicolasParajón Puenzo, Sol CarolinaMartín, Sandra ElizabethArsineBiphenylPalladiumLigandshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A versatile and efficient approach for the synthesis of new biphenyl-based arsine ligands, by a Pd-catalyzed arsination to introduce the -AsPh2 moiety, and then a Suzuki-Miyaura cross-coupling for biaryl construction is reported. By Pd-catalyzed arsination with n-Bu3SnAsPh2 (1), (2-bromophenyl)diphenylarsine (2, 83%) was obtained. The Suzuki-Miyaura reaction between the bromoarsine 2 and aryl boronic acids bearing different substituents provided biarylarsine ligands (80-99%). The efficiency of catalysts derived from the new biarylarsine ligands was evaluated in the Pd-catalyzed arsination with perfluoroalkyl iodides (RfI). Outstanding activities of catalysts derived from Pd/methoxybiarylarsine ligands were found in this coupling reaction affording perfluoroalkyl arsines in very good yields (57-100%). © 2011 The Royal Society of Chemistry.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; ArgentinaFil: Lanteri, Mario Nicolas. 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: Parajón Puenzo, Sol Carolina. 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; ArgentinaRoyal Society of Chemistry2011-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/62006Uberman, Paula Marina; Lanteri, Mario Nicolas; Parajón Puenzo, Sol Carolina; Martín, Sandra Elizabeth; Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination; Royal Society of Chemistry; Dalton Transactions; 40; 36; 9-2011; 9229-92371477-9226CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c1dt10207ainfo:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/Content/ArticleLanding/2011/DT/c1dt10207a#!divAbstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:00:26Zoai:ri.conicet.gov.ar:11336/62006instacron: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:34982025-10-15 15:00:26.841CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination
title Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination
spellingShingle Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination
Uberman, Paula Marina
Arsine
Biphenyl
Palladium
Ligands
title_short Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination
title_full Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination
title_fullStr Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination
title_full_unstemmed Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination
title_sort Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination
dc.creator.none.fl_str_mv Uberman, Paula Marina
Lanteri, Mario Nicolas
Parajón Puenzo, Sol Carolina
Martín, Sandra Elizabeth
author Uberman, Paula Marina
author_facet Uberman, Paula Marina
Lanteri, Mario Nicolas
Parajón Puenzo, Sol Carolina
Martín, Sandra Elizabeth
author_role author
author2 Lanteri, Mario Nicolas
Parajón Puenzo, Sol Carolina
Martín, Sandra Elizabeth
author2_role author
author
author
dc.subject.none.fl_str_mv Arsine
Biphenyl
Palladium
Ligands
topic Arsine
Biphenyl
Palladium
Ligands
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 versatile and efficient approach for the synthesis of new biphenyl-based arsine ligands, by a Pd-catalyzed arsination to introduce the -AsPh2 moiety, and then a Suzuki-Miyaura cross-coupling for biaryl construction is reported. By Pd-catalyzed arsination with n-Bu3SnAsPh2 (1), (2-bromophenyl)diphenylarsine (2, 83%) was obtained. The Suzuki-Miyaura reaction between the bromoarsine 2 and aryl boronic acids bearing different substituents provided biarylarsine ligands (80-99%). The efficiency of catalysts derived from the new biarylarsine ligands was evaluated in the Pd-catalyzed arsination with perfluoroalkyl iodides (RfI). Outstanding activities of catalysts derived from Pd/methoxybiarylarsine ligands were found in this coupling reaction affording perfluoroalkyl arsines in very good yields (57-100%). © 2011 The Royal Society of Chemistry.
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: Lanteri, Mario Nicolas. 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: Parajón Puenzo, Sol Carolina. 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 A versatile and efficient approach for the synthesis of new biphenyl-based arsine ligands, by a Pd-catalyzed arsination to introduce the -AsPh2 moiety, and then a Suzuki-Miyaura cross-coupling for biaryl construction is reported. By Pd-catalyzed arsination with n-Bu3SnAsPh2 (1), (2-bromophenyl)diphenylarsine (2, 83%) was obtained. The Suzuki-Miyaura reaction between the bromoarsine 2 and aryl boronic acids bearing different substituents provided biarylarsine ligands (80-99%). The efficiency of catalysts derived from the new biarylarsine ligands was evaluated in the Pd-catalyzed arsination with perfluoroalkyl iodides (RfI). Outstanding activities of catalysts derived from Pd/methoxybiarylarsine ligands were found in this coupling reaction affording perfluoroalkyl arsines in very good yields (57-100%). © 2011 The Royal Society of Chemistry.
publishDate 2011
dc.date.none.fl_str_mv 2011-09
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/11336/62006
Uberman, Paula Marina; Lanteri, Mario Nicolas; Parajón Puenzo, Sol Carolina; Martín, Sandra Elizabeth; Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination; Royal Society of Chemistry; Dalton Transactions; 40; 36; 9-2011; 9229-9237
1477-9226
CONICET Digital
CONICET
url http://hdl.handle.net/11336/62006
identifier_str_mv Uberman, Paula Marina; Lanteri, Mario Nicolas; Parajón Puenzo, Sol Carolina; Martín, Sandra Elizabeth; Synthesis of biphenyl-based arsine ligands by Suzuki-Miyaura coupling and their application to Pd-catalyzed arsination; Royal Society of Chemistry; Dalton Transactions; 40; 36; 9-2011; 9229-9237
1477-9226
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/c1dt10207a
info:eu-repo/semantics/altIdentifier/url/https://pubs.rsc.org/en/Content/ArticleLanding/2011/DT/c1dt10207a#!divAbstract
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
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
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_ 1846083143566622720
score 13.22299

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