Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes

The functionalization of alkynes by Au (N-heterocyclic carbene, NHC) complexes via the hydrophenoxylation reaction is a paradigm for the discussion between mono and dual metal catalysis. With the aim of mimicking the framework containing two gold units, achieved with molecular boxes, two NHC ligands...

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Autores: Escayola Gordils, Sílvia, Poater i Teixidor, Jordi, Ramos, Miguel, Luque Urrutia, Jesús Antonio, Duran i Carpintero, Josep, Simon i Rabasseda, Sílvia, Solà i Puig, Miquel, Cavallo, Luigi, Nolan, Steven P., Poater Teixidor, Albert
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:España
Recursos:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/19746
Acesso em linha:http://hdl.handle.net/10256/19746
Access Level:acceso abierto
Palavra-chave:Alquins
Alkynes
Catalitzadors metàl·lics
Metal catalysts
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spelling Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynesEscayola Gordils, SílviaPoater i Teixidor, JordiRamos, MiguelLuque Urrutia, Jesús AntonioDuran i Carpintero, JosepSimon i Rabasseda, SílviaSolà i Puig, MiquelCavallo, LuigiNolan, Steven P.Poater Teixidor, AlbertAlquinsAlkynesCatalitzadors metàl·licsMetal catalystsThe functionalization of alkynes by Au (N-heterocyclic carbene, NHC) complexes via the hydrophenoxylation reaction is a paradigm for the discussion between mono and dual metal catalysis. With the aim of mimicking the framework containing two gold units, achieved with molecular boxes, two NHC ligands were joined here with a chelated chain and this motif was examined in the hydrophenoxylation/hydroalkoxylation reactions through DFT calculations. This synthetic motif transforms the standard hydrophenoxylation intermolecular reaction from an inter- into an intra-molecular nucleophilic attack, when forming the C–O bond. Various chain lengths were tested with regard to the coordination of the alkyne to the cationic NHC-gold(I) centerInstitucio Catalana de Recerca i Estudis Avançats (ICREA), Grant/Award Number: ICREA Academia 2019; Generalitat de Catalunya, Grant/Award Numbers: 2017SGR348, 2017SGR39; Ministerio de Economía y Competitividad (MINECO) of Spain, Grant/Award Numbers: CTQ2017-85341-P, MDM-2017-0767, PGC2018-097722-B-I00, PID-2019-106830GB-I00, PID2020-113711GB-I00Open Access funding provided thanks to the CRUE-CSIC agreement with WileyWileyAgencia Estatal de Investigación2021info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionpeer-reviewedapplication/pdfhttp://hdl.handle.net/10256/19746http://hdl.handle.net/10256/19746Applied Organometallic Chemistry, 2021, vol. 35, núm. 10, p. e6362Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1002/aoc.6362info:eu-repo/semantics/altIdentifier/issn/0268-2605info:eu-repo/semantics/altIdentifier/eissn/1099-0739info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-Pinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-097722-B-I00Attribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:10256/197462026-05-29T05:05:01Z
dc.title.none.fl_str_mv Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes
title Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes
spellingShingle Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes
Escayola Gordils, Sílvia
Alquins
Alkynes
Catalitzadors metàl·lics
Metal catalysts
title_short Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes
title_full Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes
title_fullStr Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes
title_full_unstemmed Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes
title_sort Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes
dc.creator.none.fl_str_mv Escayola Gordils, Sílvia
Poater i Teixidor, Jordi
Ramos, Miguel
Luque Urrutia, Jesús Antonio
Duran i Carpintero, Josep
Simon i Rabasseda, Sílvia
Solà i Puig, Miquel
Cavallo, Luigi
Nolan, Steven P.
Poater Teixidor, Albert
author Escayola Gordils, Sílvia
author_facet Escayola Gordils, Sílvia
Poater i Teixidor, Jordi
Ramos, Miguel
Luque Urrutia, Jesús Antonio
Duran i Carpintero, Josep
Simon i Rabasseda, Sílvia
Solà i Puig, Miquel
Cavallo, Luigi
Nolan, Steven P.
Poater Teixidor, Albert
author_role author
author2 Poater i Teixidor, Jordi
Ramos, Miguel
Luque Urrutia, Jesús Antonio
Duran i Carpintero, Josep
Simon i Rabasseda, Sílvia
Solà i Puig, Miquel
Cavallo, Luigi
Nolan, Steven P.
Poater Teixidor, Albert
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Agencia Estatal de Investigación
dc.subject.none.fl_str_mv Alquins
Alkynes
Catalitzadors metàl·lics
Metal catalysts
topic Alquins
Alkynes
Catalitzadors metàl·lics
Metal catalysts
description The functionalization of alkynes by Au (N-heterocyclic carbene, NHC) complexes via the hydrophenoxylation reaction is a paradigm for the discussion between mono and dual metal catalysis. With the aim of mimicking the framework containing two gold units, achieved with molecular boxes, two NHC ligands were joined here with a chelated chain and this motif was examined in the hydrophenoxylation/hydroalkoxylation reactions through DFT calculations. This synthetic motif transforms the standard hydrophenoxylation intermolecular reaction from an inter- into an intra-molecular nucleophilic attack, when forming the C–O bond. Various chain lengths were tested with regard to the coordination of the alkyne to the cationic NHC-gold(I) center
publishDate 2021
dc.date.none.fl_str_mv 2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
peer-reviewed
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/19746
http://hdl.handle.net/10256/19746
url http://hdl.handle.net/10256/19746
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/aoc.6362
info:eu-repo/semantics/altIdentifier/issn/0268-2605
info:eu-repo/semantics/altIdentifier/eissn/1099-0739
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-P
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-097722-B-I00
dc.rights.none.fl_str_mv Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv Applied Organometallic Chemistry, 2021, vol. 35, núm. 10, p. e6362
Articles publicats (D-Q)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812429

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