Efficient gold(I) acyclic diaminocarbenes for the synthesis of propargylamines and indolizines

Mononuclear gold(I) acyclic diaminocarbenes (ADCs) were prepared by the reaction of 1,2-cyclohexanediamine with the corresponding isocyanide complexes [AuCl(CNR)] (R = Cy, tBu). The three-component coupling of aldehydes, amines, and alkynes was investigated by using these gold(I) ADC complexes. The...

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Autores: Aliaga-Lavrijsen, Mélanie, Herrera, Raquel P., Villacampa, M. Dolores, Gimeno, M. Concepción
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2018
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/186580
Acceso en línea:http://hdl.handle.net/10261/186580
Access Level:acceso abierto
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spelling Efficient gold(I) acyclic diaminocarbenes for the synthesis of propargylamines and indolizinesAliaga-Lavrijsen, MélanieHerrera, Raquel P.Villacampa, M. DoloresGimeno, M. ConcepciónMononuclear gold(I) acyclic diaminocarbenes (ADCs) were prepared by the reaction of 1,2-cyclohexanediamine with the corresponding isocyanide complexes [AuCl(CNR)] (R = Cy, tBu). The three-component coupling of aldehydes, amines, and alkynes was investigated by using these gold(I) ADC complexes. The new gold(I) metal complexes are highly efficient catalysts for the synthesis of propargylamines and indolizines in the absence of solvent and in mild conditions. This method affords the corresponding final products with excellent yields in short reaction times. Additionally, chiral gold(I) complexes with ADCs have been prepared and tried in the enantioselective synthesis of propargylamines.The authors thank the Ministerio de Economía y Competitividad (MINECO/FEDER CTQ2016-75816-C2-1-P and CTQ2017-88091-P) and Gobierno de Aragón-Fondo Social Europeo (E07_17R) for the financial support of our research. M.A.-L. thanks the MINECO for a predoctoral fellowship.Peer reviewedAmerican Chemical SocietyMinisterio de Economía y Competitividad (España)Agencia Estatal de Investigación (España)Ministerio de Ciencia, Innovación y Universidades (España)Gobierno de AragónEuropean CommissionHerrera, Raquel P. [0000-0002-5244-9569]Gimeno, M. Concepción [0000-0003-0553-0695]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201920192018info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/186580reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#CTQ2017-88091-P/AEI/10.13039/501100011033info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-75816-C2-1-Pinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-88091-Phttps://doi.org/10.1021/acsomega.8b01352Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1865802026-05-22T06:33:51Z
dc.title.none.fl_str_mv Efficient gold(I) acyclic diaminocarbenes for the synthesis of propargylamines and indolizines
title Efficient gold(I) acyclic diaminocarbenes for the synthesis of propargylamines and indolizines
spellingShingle Efficient gold(I) acyclic diaminocarbenes for the synthesis of propargylamines and indolizines
Aliaga-Lavrijsen, Mélanie
title_short Efficient gold(I) acyclic diaminocarbenes for the synthesis of propargylamines and indolizines
title_full Efficient gold(I) acyclic diaminocarbenes for the synthesis of propargylamines and indolizines
title_fullStr Efficient gold(I) acyclic diaminocarbenes for the synthesis of propargylamines and indolizines
title_full_unstemmed Efficient gold(I) acyclic diaminocarbenes for the synthesis of propargylamines and indolizines
title_sort Efficient gold(I) acyclic diaminocarbenes for the synthesis of propargylamines and indolizines
dc.creator.none.fl_str_mv Aliaga-Lavrijsen, Mélanie
Herrera, Raquel P.
Villacampa, M. Dolores
Gimeno, M. Concepción
author Aliaga-Lavrijsen, Mélanie
author_facet Aliaga-Lavrijsen, Mélanie
Herrera, Raquel P.
Villacampa, M. Dolores
Gimeno, M. Concepción
author_role author
author2 Herrera, Raquel P.
Villacampa, M. Dolores
Gimeno, M. Concepción
author2_role author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Agencia Estatal de Investigación (España)
Ministerio de Ciencia, Innovación y Universidades (España)
Gobierno de Aragón
European Commission
Herrera, Raquel P. [0000-0002-5244-9569]
Gimeno, M. Concepción [0000-0003-0553-0695]
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description Mononuclear gold(I) acyclic diaminocarbenes (ADCs) were prepared by the reaction of 1,2-cyclohexanediamine with the corresponding isocyanide complexes [AuCl(CNR)] (R = Cy, tBu). The three-component coupling of aldehydes, amines, and alkynes was investigated by using these gold(I) ADC complexes. The new gold(I) metal complexes are highly efficient catalysts for the synthesis of propargylamines and indolizines in the absence of solvent and in mild conditions. This method affords the corresponding final products with excellent yields in short reaction times. Additionally, chiral gold(I) complexes with ADCs have been prepared and tried in the enantioselective synthesis of propargylamines.
publishDate 2018
dc.date.none.fl_str_mv 2018
2019
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/186580
url http://hdl.handle.net/10261/186580
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#
#PLACEHOLDER_PARENT_METADATA_VALUE#
CTQ2017-88091-P/AEI/10.13039/501100011033
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-75816-C2-1-P
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-88091-P
https://doi.org/10.1021/acsomega.8b01352
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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