Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations

Autores
Rossi, Roberto Arturo
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The SRN1 reactions of trimethylstannyl and triphenylstannyl anions, and other tin nucleophiles with haloarenes are quite versatile. Thus, the SRN1 mechanism can afford triorganylstannyl aromatic compounds which otherwise would be synthesized by routes employing harsher reaction conditions. The sequence SRN1-Pd-catalysis is a powerful synthetic tool, and the scope of the reaction is unlimited owing to the nature of the sequence, i.e. ArX → ArSnR3 → ArAr, which can be iteratively repeated when appropriate substituted substrates are chosen. From stannanes obtained by the SRN1 reaction, it is possible to obtain by electrophilic reactions aromatic ketones, or through transmetalation reactions to produce boronic acids that can be used in Suzuki reactions. Using the novel dianion Me2Sn−2, it is possible to synthesize Me2SnAr2, which by Cu catalysis reaction affords Ar–Ar through homocoupling reactions. By a new methodology, organotin compounds with a Sn- heteroatom bond can be obtained and by Stille reactions aryl phosphines, arsines, stibines and selenides can be synthetized, all in one-pot reaction. The triarylarsines can be used as ligands in cross-coupling reactions. From vinyl chlorides, it is possible to obtain vinylic stannanes, which by cross-coupling reactions afford aryl substituted alkenes.
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
Materia
Srn1
Stannanes
Stille
Triarylphosphines
Triarylarsines
Vinylstannane
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:11336/31355
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformationsRossi, Roberto ArturoSrn1StannanesStilleTriarylphosphinesTriarylarsinesVinylstannanehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The SRN1 reactions of trimethylstannyl and triphenylstannyl anions, and other tin nucleophiles with haloarenes are quite versatile. Thus, the SRN1 mechanism can afford triorganylstannyl aromatic compounds which otherwise would be synthesized by routes employing harsher reaction conditions. The sequence SRN1-Pd-catalysis is a powerful synthetic tool, and the scope of the reaction is unlimited owing to the nature of the sequence, i.e. ArX → ArSnR3 → ArAr, which can be iteratively repeated when appropriate substituted substrates are chosen. From stannanes obtained by the SRN1 reaction, it is possible to obtain by electrophilic reactions aromatic ketones, or through transmetalation reactions to produce boronic acids that can be used in Suzuki reactions. Using the novel dianion Me2Sn−2, it is possible to synthesize Me2SnAr2, which by Cu catalysis reaction affords Ar–Ar through homocoupling reactions. By a new methodology, organotin compounds with a Sn- heteroatom bond can be obtained and by Stille reactions aryl phosphines, arsines, stibines and selenides can be synthetized, all in one-pot reaction. The triarylarsines can be used as ligands in cross-coupling reactions. From vinyl chlorides, it is possible to obtain vinylic stannanes, which by cross-coupling reactions afford aryl substituted alkenes.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; ArgentinaElsevier Science Sa2014-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/31355Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations; Elsevier Science Sa; Journal of Organometallic Chemistry; 751; 1-2014; 201-2120022-328XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jorganchem.2013.07.049info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0022328X13005561info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:49:46Zoai:ri.conicet.gov.ar:11336/31355instacron: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 09:49:47.178CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations
title Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations
spellingShingle Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations
Rossi, Roberto Arturo
Srn1
Stannanes
Stille
Triarylphosphines
Triarylarsines
Vinylstannane
title_short Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations
title_full Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations
title_fullStr Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations
title_full_unstemmed Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations
title_sort Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations
dc.creator.none.fl_str_mv Rossi, Roberto Arturo
author Rossi, Roberto Arturo
author_facet Rossi, Roberto Arturo
author_role author
dc.subject.none.fl_str_mv Srn1
Stannanes
Stille
Triarylphosphines
Triarylarsines
Vinylstannane
topic Srn1
Stannanes
Stille
Triarylphosphines
Triarylarsines
Vinylstannane
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The SRN1 reactions of trimethylstannyl and triphenylstannyl anions, and other tin nucleophiles with haloarenes are quite versatile. Thus, the SRN1 mechanism can afford triorganylstannyl aromatic compounds which otherwise would be synthesized by routes employing harsher reaction conditions. The sequence SRN1-Pd-catalysis is a powerful synthetic tool, and the scope of the reaction is unlimited owing to the nature of the sequence, i.e. ArX → ArSnR3 → ArAr, which can be iteratively repeated when appropriate substituted substrates are chosen. From stannanes obtained by the SRN1 reaction, it is possible to obtain by electrophilic reactions aromatic ketones, or through transmetalation reactions to produce boronic acids that can be used in Suzuki reactions. Using the novel dianion Me2Sn−2, it is possible to synthesize Me2SnAr2, which by Cu catalysis reaction affords Ar–Ar through homocoupling reactions. By a new methodology, organotin compounds with a Sn- heteroatom bond can be obtained and by Stille reactions aryl phosphines, arsines, stibines and selenides can be synthetized, all in one-pot reaction. The triarylarsines can be used as ligands in cross-coupling reactions. From vinyl chlorides, it is possible to obtain vinylic stannanes, which by cross-coupling reactions afford aryl substituted alkenes.
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
description The SRN1 reactions of trimethylstannyl and triphenylstannyl anions, and other tin nucleophiles with haloarenes are quite versatile. Thus, the SRN1 mechanism can afford triorganylstannyl aromatic compounds which otherwise would be synthesized by routes employing harsher reaction conditions. The sequence SRN1-Pd-catalysis is a powerful synthetic tool, and the scope of the reaction is unlimited owing to the nature of the sequence, i.e. ArX → ArSnR3 → ArAr, which can be iteratively repeated when appropriate substituted substrates are chosen. From stannanes obtained by the SRN1 reaction, it is possible to obtain by electrophilic reactions aromatic ketones, or through transmetalation reactions to produce boronic acids that can be used in Suzuki reactions. Using the novel dianion Me2Sn−2, it is possible to synthesize Me2SnAr2, which by Cu catalysis reaction affords Ar–Ar through homocoupling reactions. By a new methodology, organotin compounds with a Sn- heteroatom bond can be obtained and by Stille reactions aryl phosphines, arsines, stibines and selenides can be synthetized, all in one-pot reaction. The triarylarsines can be used as ligands in cross-coupling reactions. From vinyl chlorides, it is possible to obtain vinylic stannanes, which by cross-coupling reactions afford aryl substituted alkenes.
publishDate 2014
dc.date.none.fl_str_mv 2014-01
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/11336/31355
Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations; Elsevier Science Sa; Journal of Organometallic Chemistry; 751; 1-2014; 201-212
0022-328X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/31355
identifier_str_mv Recent advances in the synthesis of stannanes and the scope of theirposterior chemical transformations; Elsevier Science Sa; Journal of Organometallic Chemistry; 751; 1-2014; 201-212
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/doi/10.1016/j.jorganchem.2013.07.049
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0022328X13005561
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 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 13.070432

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