Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand

Autores
Cristóbal Lecina, Edgar; Costantino, Andrea Rosana; Grabulosa, Arnald; Riera, Antoni; Verdaguer, Xavier
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The asymmetric Pauson–Khand reaction catalyzed by [Rh(COD)(MaxPHOS)]BF4 is described. Several 1,6-enynes have been chosen as model substrates affording moderate yields and selectivities of up to 86% ee. Besides binap-type ligands, we have demonstrated that the P-stereogenic C1-symmetry small-bite-angle ligand MaxPHOS is a viable ligand in this process. The formation of [2+2+2] cycloaddition compounds has shown to be a competitive process. A mechanism is proposed to account for the observed results. The intermediate rhodium dicarbonyl complex 6 was synthesized, and its solid-state structure was elucidated by X-ray crystallography.
Fil: Cristóbal Lecina, Edgar. Barcelona Institute of Science and Technology; España
Fil: Costantino, Andrea Rosana. Barcelona Institute of Science and Technology; España. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Grabulosa, Arnald. Universidad de Barcelona; España
Fil: Riera, Antoni. Barcelona Institute of Science and Technology; España
Fil: Verdaguer, Xavier. Universidad de Barcelona; España. Barcelona Institute of Science and Technology; España
Materia
Rhodium Catalyzed
Pauson Khand
P-Stereogenic C1 Diphosphine Ligand
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:11336/40539
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine LigandCristóbal Lecina, EdgarCostantino, Andrea RosanaGrabulosa, ArnaldRiera, AntoniVerdaguer, XavierRhodium CatalyzedPauson KhandP-Stereogenic C1 Diphosphine Ligandhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The asymmetric Pauson–Khand reaction catalyzed by [Rh(COD)(MaxPHOS)]BF4 is described. Several 1,6-enynes have been chosen as model substrates affording moderate yields and selectivities of up to 86% ee. Besides binap-type ligands, we have demonstrated that the P-stereogenic C1-symmetry small-bite-angle ligand MaxPHOS is a viable ligand in this process. The formation of [2+2+2] cycloaddition compounds has shown to be a competitive process. A mechanism is proposed to account for the observed results. The intermediate rhodium dicarbonyl complex 6 was synthesized, and its solid-state structure was elucidated by X-ray crystallography.Fil: Cristóbal Lecina, Edgar. Barcelona Institute of Science and Technology; EspañaFil: Costantino, Andrea Rosana. Barcelona Institute of Science and Technology; España. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Grabulosa, Arnald. Universidad de Barcelona; EspañaFil: Riera, Antoni. Barcelona Institute of Science and Technology; EspañaFil: Verdaguer, Xavier. Universidad de Barcelona; España. Barcelona Institute of Science and Technology; EspañaAmerican Chemical Society2015-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/40539Cristóbal Lecina, Edgar; Costantino, Andrea Rosana; Grabulosa, Arnald; Riera, Antoni; Verdaguer, Xavier; Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand; American Chemical Society; Organometallics; 34; 20; 9-2015; 4989-49930276-7333CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.organomet.5b00576info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.organomet.5b00576info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:59:17Zoai:ri.conicet.gov.ar:11336/40539instacron: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 09:59:17.477CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand
title Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand
spellingShingle Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand
Cristóbal Lecina, Edgar
Rhodium Catalyzed
Pauson Khand
P-Stereogenic C1 Diphosphine Ligand
title_short Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand
title_full Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand
title_fullStr Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand
title_full_unstemmed Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand
title_sort Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand
dc.creator.none.fl_str_mv Cristóbal Lecina, Edgar
Costantino, Andrea Rosana
Grabulosa, Arnald
Riera, Antoni
Verdaguer, Xavier
author Cristóbal Lecina, Edgar
author_facet Cristóbal Lecina, Edgar
Costantino, Andrea Rosana
Grabulosa, Arnald
Riera, Antoni
Verdaguer, Xavier
author_role author
author2 Costantino, Andrea Rosana
Grabulosa, Arnald
Riera, Antoni
Verdaguer, Xavier
author2_role author
author
author
author
dc.subject.none.fl_str_mv Rhodium Catalyzed
Pauson Khand
P-Stereogenic C1 Diphosphine Ligand
topic Rhodium Catalyzed
Pauson Khand
P-Stereogenic C1 Diphosphine Ligand
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 asymmetric Pauson–Khand reaction catalyzed by [Rh(COD)(MaxPHOS)]BF4 is described. Several 1,6-enynes have been chosen as model substrates affording moderate yields and selectivities of up to 86% ee. Besides binap-type ligands, we have demonstrated that the P-stereogenic C1-symmetry small-bite-angle ligand MaxPHOS is a viable ligand in this process. The formation of [2+2+2] cycloaddition compounds has shown to be a competitive process. A mechanism is proposed to account for the observed results. The intermediate rhodium dicarbonyl complex 6 was synthesized, and its solid-state structure was elucidated by X-ray crystallography.
Fil: Cristóbal Lecina, Edgar. Barcelona Institute of Science and Technology; España
Fil: Costantino, Andrea Rosana. Barcelona Institute of Science and Technology; España. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Grabulosa, Arnald. Universidad de Barcelona; España
Fil: Riera, Antoni. Barcelona Institute of Science and Technology; España
Fil: Verdaguer, Xavier. Universidad de Barcelona; España. Barcelona Institute of Science and Technology; España
description The asymmetric Pauson–Khand reaction catalyzed by [Rh(COD)(MaxPHOS)]BF4 is described. Several 1,6-enynes have been chosen as model substrates affording moderate yields and selectivities of up to 86% ee. Besides binap-type ligands, we have demonstrated that the P-stereogenic C1-symmetry small-bite-angle ligand MaxPHOS is a viable ligand in this process. The formation of [2+2+2] cycloaddition compounds has shown to be a competitive process. A mechanism is proposed to account for the observed results. The intermediate rhodium dicarbonyl complex 6 was synthesized, and its solid-state structure was elucidated by X-ray crystallography.
publishDate 2015
dc.date.none.fl_str_mv 2015-09
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/11336/40539
Cristóbal Lecina, Edgar; Costantino, Andrea Rosana; Grabulosa, Arnald; Riera, Antoni; Verdaguer, Xavier; Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand; American Chemical Society; Organometallics; 34; 20; 9-2015; 4989-4993
0276-7333
CONICET Digital
CONICET
url http://hdl.handle.net/11336/40539
identifier_str_mv Cristóbal Lecina, Edgar; Costantino, Andrea Rosana; Grabulosa, Arnald; Riera, Antoni; Verdaguer, Xavier; Rhodium-Catalyzed Pauson-Khand Reaction Using a Small-Bite- Angle P-Stereogenic C1-Diphosphine Ligand; American Chemical Society; Organometallics; 34; 20; 9-2015; 4989-4993
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/acs.organomet.5b00576
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.organomet.5b00576
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 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
_version_ 1842269572788387840
score 13.13397

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