Dehydrogenative addition of aldehydes to a mixed NHC-osmium-phosphine hydroxide complex: formation of carboxylate derivatives

The addition of the O–H bond of [OsH(OH)(≡CPh)(IPr)(PiPr3)]OTf (1; IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolylidene, OTf = CF3SO3) to the C–Hα bond of aldehydes is reported. Complex 1 reacts with n-propanal, acrolein, cinnamaldehyde, and benzaldehyde to give the carboxylate-hydride-alkylidyne der...

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Autores: Buil, María L., Cardo, Juan F., Esteruelas, Miguel A., Oñate, Enrique
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/134669
Acceso en línea:http://hdl.handle.net/10261/134669
Access Level:acceso abierto
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spelling Dehydrogenative addition of aldehydes to a mixed NHC-osmium-phosphine hydroxide complex: formation of carboxylate derivativesBuil, María L.Cardo, Juan F.Esteruelas, Miguel A.Oñate, EnriqueThe addition of the O–H bond of [OsH(OH)(≡CPh)(IPr)(PiPr3)]OTf (1; IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolylidene, OTf = CF3SO3) to the C–Hα bond of aldehydes is reported. Complex 1 reacts with n-propanal, acrolein, cinnamaldehyde, and benzaldehyde to give the carboxylate-hydride-alkylidyne derivatives [OsH(κ2-O2CR)(≡CPh)(IPr)(PiPr3)]OTf (R = Et (2), CH═CH2 (3), CH═CHPh (4), Ph (5)) and H2. Complexes 2, 4, and 5 afford the alkylidenes [Os(κ2-O2CR)(CO)(═CHPh)(IPr)(PiPr3)]OTf (R = Et (6), CH═CHPh (7), Ph (8)) under a CO atmosphere.Financial support from the Spanish MINECO (Projects CTQ2014-52799-P, Red de Excelencia Consolider CTQ2014-51912-REDC), the DGA (E35), and the European Social Fund (FSE) is acknowledged. J.J.F.C. acknowledges support via a predoctoral fellowship from the DGA.Peer reviewedAmerican Chemical SocietyDiputación General de AragónMinisterio de Economía y Competitividad (España)European CommissionConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201620162016info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/134669reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-52799-Pinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-51912-REDChttp://dx.doi.org/10.1021/acs.organomet.6b00396Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1346692026-05-22T06:33:51Z
dc.title.none.fl_str_mv Dehydrogenative addition of aldehydes to a mixed NHC-osmium-phosphine hydroxide complex: formation of carboxylate derivatives
title Dehydrogenative addition of aldehydes to a mixed NHC-osmium-phosphine hydroxide complex: formation of carboxylate derivatives
spellingShingle Dehydrogenative addition of aldehydes to a mixed NHC-osmium-phosphine hydroxide complex: formation of carboxylate derivatives
Buil, María L.
title_short Dehydrogenative addition of aldehydes to a mixed NHC-osmium-phosphine hydroxide complex: formation of carboxylate derivatives
title_full Dehydrogenative addition of aldehydes to a mixed NHC-osmium-phosphine hydroxide complex: formation of carboxylate derivatives
title_fullStr Dehydrogenative addition of aldehydes to a mixed NHC-osmium-phosphine hydroxide complex: formation of carboxylate derivatives
title_full_unstemmed Dehydrogenative addition of aldehydes to a mixed NHC-osmium-phosphine hydroxide complex: formation of carboxylate derivatives
title_sort Dehydrogenative addition of aldehydes to a mixed NHC-osmium-phosphine hydroxide complex: formation of carboxylate derivatives
dc.creator.none.fl_str_mv Buil, María L.
Cardo, Juan F.
Esteruelas, Miguel A.
Oñate, Enrique
author Buil, María L.
author_facet Buil, María L.
Cardo, Juan F.
Esteruelas, Miguel A.
Oñate, Enrique
author_role author
author2 Cardo, Juan F.
Esteruelas, Miguel A.
Oñate, Enrique
author2_role author
author
author
dc.contributor.none.fl_str_mv Diputación General de Aragón
Ministerio de Economía y Competitividad (España)
European Commission
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description The addition of the O–H bond of [OsH(OH)(≡CPh)(IPr)(PiPr3)]OTf (1; IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolylidene, OTf = CF3SO3) to the C–Hα bond of aldehydes is reported. Complex 1 reacts with n-propanal, acrolein, cinnamaldehyde, and benzaldehyde to give the carboxylate-hydride-alkylidyne derivatives [OsH(κ2-O2CR)(≡CPh)(IPr)(PiPr3)]OTf (R = Et (2), CH═CH2 (3), CH═CHPh (4), Ph (5)) and H2. Complexes 2, 4, and 5 afford the alkylidenes [Os(κ2-O2CR)(CO)(═CHPh)(IPr)(PiPr3)]OTf (R = Et (6), CH═CHPh (7), Ph (8)) under a CO atmosphere.
publishDate 2016
dc.date.none.fl_str_mv 2016
2016
2016
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/134669
url http://hdl.handle.net/10261/134669
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-52799-P
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-51912-REDC
http://dx.doi.org/10.1021/acs.organomet.6b00396
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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