Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives

Autores
Pérez Hincapié, Liddier Oiden; Dómina, Tomás Alberto; Fernandez, Gabriela Araceli; Silbestri, Gustavo Fabián; Testero, Sebastian Andres
Año de publicación
2024
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Hydrocarboxylationof alkyne-containing amino acid derivatives using water-soluble gold(I)–NHCcomplexes in an aqueous biphasic system at room temperature is described.Addition of silver salts is not required as the carboxylic acid group of thesubstrate is responsible for the activation of the gold catalyst at roomtemperature. Our result confirms that the steric bulk of the N-heterocyclic carbene ligands is animportant factor in both the stability and the catalytic activity of gold(I)complexes in aqueous medium, and consequently in the recycling (at least 15times without any loss of activity). The catalytic activity of our most activewater-soluble gold(I)–NHC complex has been demonstrated in thecycloisomerization of amino acids derivatives with terminal and internal alkynesin aqueous media at room temperature.
Fil: Pérez Hincapié, Liddier Oiden. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Dómina, Tomás Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Fernandez, Gabriela Araceli. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Silbestri, Gustavo Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Testero, Sebastian Andres. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Materia
HOMOGENEOUS GOLD CATALYSIS
REACTIONS IN AQUEOUS MEDIA
WATER-SOLUBLE NHC CATALYSTS
N-HETEROCYCLIC CARBENES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/265098
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/265098
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivativesPérez Hincapié, Liddier OidenDómina, Tomás AlbertoFernandez, Gabriela AraceliSilbestri, Gustavo FabiánTestero, Sebastian AndresHOMOGENEOUS GOLD CATALYSISREACTIONS IN AQUEOUS MEDIAWATER-SOLUBLE NHC CATALYSTSN-HETEROCYCLIC CARBENEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Hydrocarboxylationof alkyne-containing amino acid derivatives using water-soluble gold(I)–NHCcomplexes in an aqueous biphasic system at room temperature is described.Addition of silver salts is not required as the carboxylic acid group of thesubstrate is responsible for the activation of the gold catalyst at roomtemperature. Our result confirms that the steric bulk of the N-heterocyclic carbene ligands is animportant factor in both the stability and the catalytic activity of gold(I)complexes in aqueous medium, and consequently in the recycling (at least 15times without any loss of activity). The catalytic activity of our most activewater-soluble gold(I)–NHC complex has been demonstrated in thecycloisomerization of amino acids derivatives with terminal and internal alkynesin aqueous media at room temperature.Fil: Pérez Hincapié, Liddier Oiden. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Dómina, Tomás Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Fernandez, Gabriela Araceli. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Silbestri, Gustavo Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Testero, Sebastian Andres. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaRoyal Society of Chemistry2024-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/265098Pérez Hincapié, Liddier Oiden; Dómina, Tomás Alberto; Fernandez, Gabriela Araceli; Silbestri, Gustavo Fabián; Testero, Sebastian Andres; Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives; Royal Society of Chemistry; RSC Advances; 14; 34; 7-2024; 24643-246512046-2069CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://xlink.rsc.org/?DOI=D4RA04876Hinfo:eu-repo/semantics/altIdentifier/doi/10.1039/D4RA04876Hinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:39:02Zoai:ri.conicet.gov.ar:11336/265098instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:39:02.544CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives
title Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives
spellingShingle Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives
Pérez Hincapié, Liddier Oiden
HOMOGENEOUS GOLD CATALYSIS
REACTIONS IN AQUEOUS MEDIA
WATER-SOLUBLE NHC CATALYSTS
N-HETEROCYCLIC CARBENES
title_short Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives
title_full Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives
title_fullStr Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives
title_full_unstemmed Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives
title_sort Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives
dc.creator.none.fl_str_mv Pérez Hincapié, Liddier Oiden
Dómina, Tomás Alberto
Fernandez, Gabriela Araceli
Silbestri, Gustavo Fabián
Testero, Sebastian Andres
author Pérez Hincapié, Liddier Oiden
author_facet Pérez Hincapié, Liddier Oiden
Dómina, Tomás Alberto
Fernandez, Gabriela Araceli
Silbestri, Gustavo Fabián
Testero, Sebastian Andres
author_role author
author2 Dómina, Tomás Alberto
Fernandez, Gabriela Araceli
Silbestri, Gustavo Fabián
Testero, Sebastian Andres
author2_role author
author
author
author
dc.subject.none.fl_str_mv HOMOGENEOUS GOLD CATALYSIS
REACTIONS IN AQUEOUS MEDIA
WATER-SOLUBLE NHC CATALYSTS
N-HETEROCYCLIC CARBENES
topic HOMOGENEOUS GOLD CATALYSIS
REACTIONS IN AQUEOUS MEDIA
WATER-SOLUBLE NHC CATALYSTS
N-HETEROCYCLIC CARBENES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Hydrocarboxylationof alkyne-containing amino acid derivatives using water-soluble gold(I)–NHCcomplexes in an aqueous biphasic system at room temperature is described.Addition of silver salts is not required as the carboxylic acid group of thesubstrate is responsible for the activation of the gold catalyst at roomtemperature. Our result confirms that the steric bulk of the N-heterocyclic carbene ligands is animportant factor in both the stability and the catalytic activity of gold(I)complexes in aqueous medium, and consequently in the recycling (at least 15times without any loss of activity). The catalytic activity of our most activewater-soluble gold(I)–NHC complex has been demonstrated in thecycloisomerization of amino acids derivatives with terminal and internal alkynesin aqueous media at room temperature.
Fil: Pérez Hincapié, Liddier Oiden. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Dómina, Tomás Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Fernandez, Gabriela Araceli. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Silbestri, Gustavo Fabián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Testero, Sebastian Andres. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
description Hydrocarboxylationof alkyne-containing amino acid derivatives using water-soluble gold(I)–NHCcomplexes in an aqueous biphasic system at room temperature is described.Addition of silver salts is not required as the carboxylic acid group of thesubstrate is responsible for the activation of the gold catalyst at roomtemperature. Our result confirms that the steric bulk of the N-heterocyclic carbene ligands is animportant factor in both the stability and the catalytic activity of gold(I)complexes in aqueous medium, and consequently in the recycling (at least 15times without any loss of activity). The catalytic activity of our most activewater-soluble gold(I)–NHC complex has been demonstrated in thecycloisomerization of amino acids derivatives with terminal and internal alkynesin aqueous media at room temperature.
publishDate 2024
dc.date.none.fl_str_mv 2024-07
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/265098
Pérez Hincapié, Liddier Oiden; Dómina, Tomás Alberto; Fernandez, Gabriela Araceli; Silbestri, Gustavo Fabián; Testero, Sebastian Andres; Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives; Royal Society of Chemistry; RSC Advances; 14; 34; 7-2024; 24643-24651
2046-2069
CONICET Digital
CONICET
url http://hdl.handle.net/11336/265098
identifier_str_mv Pérez Hincapié, Liddier Oiden; Dómina, Tomás Alberto; Fernandez, Gabriela Araceli; Silbestri, Gustavo Fabián; Testero, Sebastian Andres; Unlocking the potential of water-soluble gold( i )–NHC complexes: unveiling the role of carboxylic acid in cycloisomerization of alkynyl amino acid derivatives; Royal Society of Chemistry; RSC Advances; 14; 34; 7-2024; 24643-24651
2046-2069
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://xlink.rsc.org/?DOI=D4RA04876H
info:eu-repo/semantics/altIdentifier/doi/10.1039/D4RA04876H
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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