Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters

A catalytic, versatile and atom-economical C−H functionalization process that provides a wide variety of cyclic systems featuring methyl-substituted quaternary stereocenters is described. The method relies on the use of a cationic IrI–bisphosphine catalyst, which promotes a carboxamide-assisted acti...

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Detalles Bibliográficos
Autores: Fernández Fernández, David, Gulías Costa, Moisés, Mascareñas Cid, José Luis, López García, Fernando
Tipo de recurso: artículo
Fecha de publicación:2017
País:España
Institución:Universidad de Santiago de Compostela (USC)
Repositorio:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
Idioma:inglés
OAI Identifier:oai:minerva.usc.gal:10347/15752
Acceso en línea:http://hdl.handle.net/10347/15752
Access Level:acceso abierto
Palabra clave:C−H activation
Asymmetric catalysis
Hydroalkenylation
Hydroarylation
Iridium
Materias::Investigación::23 Química::2302 Bioquímica
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spelling Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary StereocentersFernández Fernández, DavidGulías Costa, MoisésMascareñas Cid, José LuisLópez García, FernandoC−H activationAsymmetric catalysisHydroalkenylationHydroarylationIridiumMaterias::Investigación::23 Química::2302 BioquímicaA catalytic, versatile and atom-economical C−H functionalization process that provides a wide variety of cyclic systems featuring methyl-substituted quaternary stereocenters is described. The method relies on the use of a cationic IrI–bisphosphine catalyst, which promotes a carboxamide-assisted activation of an olefinic C(sp2)−H bond followed by exo-cyclization to a tethered 1,1-disubstituted alkene. The extension of the method to aromatic and heteroaromatic C−H bonds, as well as developments on an enantioselective variant, are also describedWileyUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais MolecularesUniversidade de Santiago de Compostela. Departamento de Química Orgánica20172017-07-1220172017-07-12journal articlehttp://purl.org/coar/resource_type/c_6501AMhttp://purl.org/coar/version/c_ab4af688f83e57aainfo:eu-repo/semantics/articleapplication/pdfapplication/pdfhttp://hdl.handle.net/10347/15752reponame:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostelainstname:Universidad de Santiago de Compostela (USC)InglésengEuropean Commission http://dx.doi.org/10.13039/501100000780 Seventh Framework Programme 340055Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 SAF2016-76689-Ropen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:minerva.usc.gal:10347/157522026-06-15T12:47:27Z
dc.title.none.fl_str_mv Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters
title Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters
spellingShingle Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters
Fernández Fernández, David
C−H activation
Asymmetric catalysis
Hydroalkenylation
Hydroarylation
Iridium
Materias::Investigación::23 Química::2302 Bioquímica
title_short Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters
title_full Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters
title_fullStr Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters
title_full_unstemmed Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters
title_sort Iridium(I)-Catalyzed Intramolecular Hydrocarbonation of Alkenes: Efficient Access to Cyclic Systems Bearing Quaternary Stereocenters
dc.creator.none.fl_str_mv Fernández Fernández, David
Gulías Costa, Moisés
Mascareñas Cid, José Luis
López García, Fernando
author Fernández Fernández, David
author_facet Fernández Fernández, David
Gulías Costa, Moisés
Mascareñas Cid, José Luis
López García, Fernando
author_role author
author2 Gulías Costa, Moisés
Mascareñas Cid, José Luis
López García, Fernando
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares
Universidade de Santiago de Compostela. Departamento de Química Orgánica
dc.subject.none.fl_str_mv C−H activation
Asymmetric catalysis
Hydroalkenylation
Hydroarylation
Iridium
Materias::Investigación::23 Química::2302 Bioquímica
topic C−H activation
Asymmetric catalysis
Hydroalkenylation
Hydroarylation
Iridium
Materias::Investigación::23 Química::2302 Bioquímica
description A catalytic, versatile and atom-economical C−H functionalization process that provides a wide variety of cyclic systems featuring methyl-substituted quaternary stereocenters is described. The method relies on the use of a cationic IrI–bisphosphine catalyst, which promotes a carboxamide-assisted activation of an olefinic C(sp2)−H bond followed by exo-cyclization to a tethered 1,1-disubstituted alkene. The extension of the method to aromatic and heteroaromatic C−H bonds, as well as developments on an enantioselective variant, are also described
publishDate 2017
dc.date.none.fl_str_mv 2017
2017-07-12
2017
2017-07-12
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
AM
http://purl.org/coar/version/c_ab4af688f83e57aa
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10347/15752
url http://hdl.handle.net/10347/15752
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv European Commission http://dx.doi.org/10.13039/501100000780 Seventh Framework Programme 340055
Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 SAF2016-76689-R
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
instname:Universidad de Santiago de Compostela (USC)
instname_str Universidad de Santiago de Compostela (USC)
reponame_str Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
collection Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.812455

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