Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates

The reaction of N-unprotected methylesters of phenylglycine derivatives (1a–1f) with electron-rich internal alkynes (2a–2e), catalyzed by [Ru(cymene)Cl] (10%), gives the corresponding 3,4-disubstituted isoquinoline-1-carboxylates 3 through C[sbnd]H/N[sbnd]H oxidative coupling. The C[sbnd]H bond acti...

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Detalles Bibliográficos
Autores: Ruiz Morte, Sara, Sayago, Francisco J., Cativiela, Carlos, Urriolabeitia, Esteban P.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/155864
Acceso en línea:http://hdl.handle.net/10261/155864
Access Level:acceso abierto
Palabra clave:Isoindolines
Csingle bondH activation
Isoquinolines
Amino acids
Ru-complexes
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spelling Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylatesRuiz Morte, SaraSayago, Francisco J.Cativiela, CarlosUrriolabeitia, Esteban P.IsoindolinesCsingle bondH activationIsoquinolinesAmino acidsRu-complexesThe reaction of N-unprotected methylesters of phenylglycine derivatives (1a–1f) with electron-rich internal alkynes (2a–2e), catalyzed by [Ru(cymene)Cl] (10%), gives the corresponding 3,4-disubstituted isoquinoline-1-carboxylates 3 through C[sbnd]H/N[sbnd]H oxidative coupling. The C[sbnd]H bond activation step is assisted by carboxylates, and N-fluoro-2,4,6-trimethylpyridinium triflate works as the terminal oxidant. The process shows a remarkable tolerance to the presence of diverse electron-releasing and electron-attracting functional groups at the phenyl ring of the amino acid. In addition, the reaction of phenylglycine derivatives (1a–1f) with methyl acrylate (4a) catalyzed by [Ru(cymene)Cl] (10%) under the same experimental conditions, gives the corresponding 3,N-disubstituted isoindoline-1-carboxylates 5 through C[sbnd]H/N[sbnd]H coupling. Isoindolines 5 are obtained as a mixture of diastereoisomers, with moderate to high values of diastereomeric excess (up to 80%).Funding by the Ministerio de Economia y Competitividad (MINECO) (Spain, Project CTQ2013-40855-R) and Gobierno de Aragón-Fondo Social Europeo (Spain, groups E40 and E97) is gratefully acknowledged. S.R. thanks Gobierno de Aragón for a PhD grant.Peer ReviewedElsevierMinisterio de Economía y Competitividad (España)European CommissionGobierno de AragónConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2017201720172017info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/155864reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2013-40855-Rhttps://doi.org/10.1016/j.molcata.2016.06.026Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1558642026-05-22T06:33:51Z
dc.title.none.fl_str_mv Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
title Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
spellingShingle Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
Ruiz Morte, Sara
Isoindolines
Csingle bondH activation
Isoquinolines
Amino acids
Ru-complexes
title_short Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
title_full Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
title_fullStr Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
title_full_unstemmed Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
title_sort Ru-catalyzed C-H functionalization of phenylglycine derivatives: Synthesis of isoquinoline-1-carboxylates and isoindoline-1-carboxylates
dc.creator.none.fl_str_mv Ruiz Morte, Sara
Sayago, Francisco J.
Cativiela, Carlos
Urriolabeitia, Esteban P.
author Ruiz Morte, Sara
author_facet Ruiz Morte, Sara
Sayago, Francisco J.
Cativiela, Carlos
Urriolabeitia, Esteban P.
author_role author
author2 Sayago, Francisco J.
Cativiela, Carlos
Urriolabeitia, Esteban P.
author2_role author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
European Commission
Gobierno de Aragón
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Isoindolines
Csingle bondH activation
Isoquinolines
Amino acids
Ru-complexes
topic Isoindolines
Csingle bondH activation
Isoquinolines
Amino acids
Ru-complexes
description The reaction of N-unprotected methylesters of phenylglycine derivatives (1a–1f) with electron-rich internal alkynes (2a–2e), catalyzed by [Ru(cymene)Cl] (10%), gives the corresponding 3,4-disubstituted isoquinoline-1-carboxylates 3 through C[sbnd]H/N[sbnd]H oxidative coupling. The C[sbnd]H bond activation step is assisted by carboxylates, and N-fluoro-2,4,6-trimethylpyridinium triflate works as the terminal oxidant. The process shows a remarkable tolerance to the presence of diverse electron-releasing and electron-attracting functional groups at the phenyl ring of the amino acid. In addition, the reaction of phenylglycine derivatives (1a–1f) with methyl acrylate (4a) catalyzed by [Ru(cymene)Cl] (10%) under the same experimental conditions, gives the corresponding 3,N-disubstituted isoindoline-1-carboxylates 5 through C[sbnd]H/N[sbnd]H coupling. Isoindolines 5 are obtained as a mixture of diastereoisomers, with moderate to high values of diastereomeric excess (up to 80%).
publishDate 2017
dc.date.none.fl_str_mv 2017
2017
2017
2017
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/10261/155864
url http://hdl.handle.net/10261/155864
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2013-40855-R
https://doi.org/10.1016/j.molcata.2016.06.026
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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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score 15,811543

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