MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations

Autores
Cristóbal Lecina, Edgar; Etayo, Pablo; Doran, Séan; Revés, Marc; Martín Gago, Pablo; Grabulosa, Arnald; Costantino, Andrea Rosana; Vidal Ferran, Anton; Riera, Antoni; Verdaguer, Xavier
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
MaxPHOS is an active and robust P-stereogenic ligand for asymmetric catalysis. The presence of an NH bridge between the two phosphine moieties allows the NH/PH tautomerism to take place. The neutral ligand, in which the NH form predominates, is an air-sensitive compound. However, protonation of MaxPHOS leads to the stable PH form of the ligand, in which the overall positive charge is distributed on both P centers. This protonation turns the MaxPHOS·HBF4 salt 3 into an airstable compound both in the solid state and in solution. The salt 3 is also a convenient precursor for the preparation of rhodium(I) complexes by direct ligand exchange with the complex [Rh(acac)(cod)]. Finally, the corresponding rhodium(I)-MaxPHOS complex was tested in the asymmetric hydrogenation of a wide range of substrates. The complex proved to be a highly selective and robust system in these reactions.
Fil: Cristóbal Lecina, Edgar. Institute for Research in Biomedicine ; España
Fil: Etayo, Pablo. Institut Català d'Investigació Química; España
Fil: Doran, Séan. Institute for Research in Biomedicine ; España
Fil: Revés, Marc. Institute for Research in Biomedicine ; España
Fil: Martín Gago, Pablo. Institute for Research in Biomedicine ; España
Fil: Grabulosa, Arnald. Universidad de Barcelona; España
Fil: Costantino, Andrea Rosana. Institute for Research in Biomedicine ; 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: Vidal Ferran, Anton. Institut Català d'Investigació Química; España. Institució Catalana de Recerca i Estudis Avancats; España
Fil: Riera, Antoni. Universidad de Barcelona; España. Institute for Research in Biomedicine ; España
Fil: Verdaguer, Xavier. Institute for Research in Biomedicine ; España. Universidad de Barcelona; España
Materia
Asymmetric Catalysis
Hydrogenation
P Ligands
Tautomerism
Rhodium
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:11336/31613
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/31613
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric HydrogenationsCristóbal Lecina, EdgarEtayo, PabloDoran, SéanRevés, MarcMartín Gago, PabloGrabulosa, ArnaldCostantino, Andrea RosanaVidal Ferran, AntonRiera, AntoniVerdaguer, XavierAsymmetric CatalysisHydrogenationP LigandsTautomerismRhodiumhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1MaxPHOS is an active and robust P-stereogenic ligand for asymmetric catalysis. The presence of an NH bridge between the two phosphine moieties allows the NH/PH tautomerism to take place. The neutral ligand, in which the NH form predominates, is an air-sensitive compound. However, protonation of MaxPHOS leads to the stable PH form of the ligand, in which the overall positive charge is distributed on both P centers. This protonation turns the MaxPHOS·HBF4 salt 3 into an airstable compound both in the solid state and in solution. The salt 3 is also a convenient precursor for the preparation of rhodium(I) complexes by direct ligand exchange with the complex [Rh(acac)(cod)]. Finally, the corresponding rhodium(I)-MaxPHOS complex was tested in the asymmetric hydrogenation of a wide range of substrates. The complex proved to be a highly selective and robust system in these reactions.Fil: Cristóbal Lecina, Edgar. Institute for Research in Biomedicine ; EspañaFil: Etayo, Pablo. Institut Català d'Investigació Química; EspañaFil: Doran, Séan. Institute for Research in Biomedicine ; EspañaFil: Revés, Marc. Institute for Research in Biomedicine ; EspañaFil: Martín Gago, Pablo. Institute for Research in Biomedicine ; EspañaFil: Grabulosa, Arnald. Universidad de Barcelona; EspañaFil: Costantino, Andrea Rosana. Institute for Research in Biomedicine ; 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: Vidal Ferran, Anton. Institut Català d'Investigació Química; España. Institució Catalana de Recerca i Estudis Avancats; EspañaFil: Riera, Antoni. Universidad de Barcelona; España. Institute for Research in Biomedicine ; EspañaFil: Verdaguer, Xavier. Institute for Research in Biomedicine ; España. Universidad de Barcelona; EspañaWiley VCH Verlag2014-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/31613Verdaguer, Xavier; Costantino, Andrea Rosana; Grabulosa, Arnald; Martín Gago, Pablo; Doran, Séan; Etayo, Pablo; et al.; MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations; Wiley VCH Verlag; Advanced Synthesis & Catalysis (print); 356; 4; 3-2014; 795-8041615-4150CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/adsc.201300662/abstractinfo:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201300662info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:52:28Zoai:ri.conicet.gov.ar:11336/31613instacron: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 09:52:28.781CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations
title MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations
spellingShingle MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations
Cristóbal Lecina, Edgar
Asymmetric Catalysis
Hydrogenation
P Ligands
Tautomerism
Rhodium
title_short MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations
title_full MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations
title_fullStr MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations
title_full_unstemmed MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations
title_sort MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations
dc.creator.none.fl_str_mv Cristóbal Lecina, Edgar
Etayo, Pablo
Doran, Séan
Revés, Marc
Martín Gago, Pablo
Grabulosa, Arnald
Costantino, Andrea Rosana
Vidal Ferran, Anton
Riera, Antoni
Verdaguer, Xavier
author Cristóbal Lecina, Edgar
author_facet Cristóbal Lecina, Edgar
Etayo, Pablo
Doran, Séan
Revés, Marc
Martín Gago, Pablo
Grabulosa, Arnald
Costantino, Andrea Rosana
Vidal Ferran, Anton
Riera, Antoni
Verdaguer, Xavier
author_role author
author2 Etayo, Pablo
Doran, Séan
Revés, Marc
Martín Gago, Pablo
Grabulosa, Arnald
Costantino, Andrea Rosana
Vidal Ferran, Anton
Riera, Antoni
Verdaguer, Xavier
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Asymmetric Catalysis
Hydrogenation
P Ligands
Tautomerism
Rhodium
topic Asymmetric Catalysis
Hydrogenation
P Ligands
Tautomerism
Rhodium
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv MaxPHOS is an active and robust P-stereogenic ligand for asymmetric catalysis. The presence of an NH bridge between the two phosphine moieties allows the NH/PH tautomerism to take place. The neutral ligand, in which the NH form predominates, is an air-sensitive compound. However, protonation of MaxPHOS leads to the stable PH form of the ligand, in which the overall positive charge is distributed on both P centers. This protonation turns the MaxPHOS·HBF4 salt 3 into an airstable compound both in the solid state and in solution. The salt 3 is also a convenient precursor for the preparation of rhodium(I) complexes by direct ligand exchange with the complex [Rh(acac)(cod)]. Finally, the corresponding rhodium(I)-MaxPHOS complex was tested in the asymmetric hydrogenation of a wide range of substrates. The complex proved to be a highly selective and robust system in these reactions.
Fil: Cristóbal Lecina, Edgar. Institute for Research in Biomedicine ; España
Fil: Etayo, Pablo. Institut Català d'Investigació Química; España
Fil: Doran, Séan. Institute for Research in Biomedicine ; España
Fil: Revés, Marc. Institute for Research in Biomedicine ; España
Fil: Martín Gago, Pablo. Institute for Research in Biomedicine ; España
Fil: Grabulosa, Arnald. Universidad de Barcelona; España
Fil: Costantino, Andrea Rosana. Institute for Research in Biomedicine ; 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: Vidal Ferran, Anton. Institut Català d'Investigació Química; España. Institució Catalana de Recerca i Estudis Avancats; España
Fil: Riera, Antoni. Universidad de Barcelona; España. Institute for Research in Biomedicine ; España
Fil: Verdaguer, Xavier. Institute for Research in Biomedicine ; España. Universidad de Barcelona; España
description MaxPHOS is an active and robust P-stereogenic ligand for asymmetric catalysis. The presence of an NH bridge between the two phosphine moieties allows the NH/PH tautomerism to take place. The neutral ligand, in which the NH form predominates, is an air-sensitive compound. However, protonation of MaxPHOS leads to the stable PH form of the ligand, in which the overall positive charge is distributed on both P centers. This protonation turns the MaxPHOS·HBF4 salt 3 into an airstable compound both in the solid state and in solution. The salt 3 is also a convenient precursor for the preparation of rhodium(I) complexes by direct ligand exchange with the complex [Rh(acac)(cod)]. Finally, the corresponding rhodium(I)-MaxPHOS complex was tested in the asymmetric hydrogenation of a wide range of substrates. The complex proved to be a highly selective and robust system in these reactions.
publishDate 2014
dc.date.none.fl_str_mv 2014-03
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/11336/31613
Verdaguer, Xavier; Costantino, Andrea Rosana; Grabulosa, Arnald; Martín Gago, Pablo; Doran, Séan; Etayo, Pablo; et al.; MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations; Wiley VCH Verlag; Advanced Synthesis & Catalysis (print); 356; 4; 3-2014; 795-804
1615-4150
CONICET Digital
CONICET
url http://hdl.handle.net/11336/31613
identifier_str_mv Verdaguer, Xavier; Costantino, Andrea Rosana; Grabulosa, Arnald; Martín Gago, Pablo; Doran, Séan; Etayo, Pablo; et al.; MaxPHOS Ligand: PH/NH Tautomerism and Rhodium- Catalyzed Asymmetric Hydrogenations; Wiley VCH Verlag; Advanced Synthesis & Catalysis (print); 356; 4; 3-2014; 795-804
1615-4150
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/adsc.201300662/abstract
info:eu-repo/semantics/altIdentifier/doi/10.1002/adsc.201300662
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 Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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_ 1842269161508569088
score 13.13397

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