Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides

Complex CpRuCl(PPh3)(2) catalyzes reactions of terminal alkynes with 4-picoline N-oxide and primary and secondary amines to afford the corresponding amides. The reactions occur in chlorinated solvent and aqueous medium, showing applications in peptide chemistry. Stoichiometric studies reveal that th...

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Autores: Alvarez-Perez, A., Esteruelas, M.A., Izquierdo, S., Varela, J.A., Saa, C.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
País:España
Institución:Universidad de Zaragoza
Repositorio:Zaguán. Repositorio Digital de la Universidad de Zaragoza
OAI Identifier:oai:zaguan.unizar.es:169434
Acceso en línea:http://zaguan.unizar.es/record/169434
Access Level:acceso abierto
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spelling Ruthenium-Catalyzed Oxidative Amidation of Alkynes to AmidesAlvarez-Perez, A.Esteruelas, M.A.Izquierdo, S.Varela, J.A.Saa, C.Complex CpRuCl(PPh3)(2) catalyzes reactions of terminal alkynes with 4-picoline N-oxide and primary and secondary amines to afford the corresponding amides. The reactions occur in chlorinated solvent and aqueous medium, showing applications in peptide chemistry. Stoichiometric studies reveal that the true catalysts of the processes are the vinylidene cations [CpRu(=C=CHR)(PPh3)(2)](+) which are oxidized to the Ru(eta(2)-CO)-ketenes by the N-oxide. Finally, nucleophilic additions of primary and secondary amines to the free ketenes yield the corresponding amides.2019info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://zaguan.unizar.es/record/169434reponame:Zaguán. Repositorio Digital de la Universidad de Zaragozainstname:Universidad de ZaragozaInglésinfo:eu-repo/grantAgreement/ES/DGA/E06-17Rinfo:eu-repo/grantAgreement/ES/MINECO/CTQ2014-59015-Rinfo:eu-repo/grantAgreement/ES/MINECO/CTQ2017-82935-Pinfo:eu-repo/grantAgreement/ES/MINECO/CTQ2017-87939-Rinfo:eu-repo/semantics/openAccessoai:zaguan.unizar.es:1694342026-05-29T13:59:51Z
dc.title.none.fl_str_mv Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
title Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
spellingShingle Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
Alvarez-Perez, A.
title_short Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
title_full Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
title_fullStr Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
title_full_unstemmed Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
title_sort Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides
dc.creator.none.fl_str_mv Alvarez-Perez, A.
Esteruelas, M.A.
Izquierdo, S.
Varela, J.A.
Saa, C.
author Alvarez-Perez, A.
author_facet Alvarez-Perez, A.
Esteruelas, M.A.
Izquierdo, S.
Varela, J.A.
Saa, C.
author_role author
author2 Esteruelas, M.A.
Izquierdo, S.
Varela, J.A.
Saa, C.
author2_role author
author
author
author
description Complex CpRuCl(PPh3)(2) catalyzes reactions of terminal alkynes with 4-picoline N-oxide and primary and secondary amines to afford the corresponding amides. The reactions occur in chlorinated solvent and aqueous medium, showing applications in peptide chemistry. Stoichiometric studies reveal that the true catalysts of the processes are the vinylidene cations [CpRu(=C=CHR)(PPh3)(2)](+) which are oxidized to the Ru(eta(2)-CO)-ketenes by the N-oxide. Finally, nucleophilic additions of primary and secondary amines to the free ketenes yield the corresponding amides.
publishDate 2019
dc.date.none.fl_str_mv 2019
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info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://zaguan.unizar.es/record/169434
url http://zaguan.unizar.es/record/169434
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/ES/DGA/E06-17R
info:eu-repo/grantAgreement/ES/MINECO/CTQ2014-59015-R
info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-82935-P
info:eu-repo/grantAgreement/ES/MINECO/CTQ2017-87939-R
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
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publisher.none.fl_str_mv
dc.source.none.fl_str_mv reponame:Zaguán. Repositorio Digital de la Universidad de Zaragoza
instname:Universidad de Zaragoza
instname_str Universidad de Zaragoza
reponame_str Zaguán. Repositorio Digital de la Universidad de Zaragoza
collection Zaguán. Repositorio Digital de la Universidad de Zaragoza
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