Squaramide‐IRMOF‐16 analogue for catalysis of solvent‐free, epoxide ring‐opening tandem and multicomponent reactions

Tandem and multicomponent one‐pot reactions are highly attractive because they enable synthesis of target molecules in a single reaction vessel. However, they are difficult to control, as they can lead to the formation of many undesired side‐products. Herein we report the use of metal‐organic framew...

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Detalhes bibliográficos
Autores: Vignatti, Claudia, Luis-Barrera, Javier, Guillerm, Vincent, Imaz, Inhar, Mas-Ballesté, Rubén, Alemán, José, Maspoch, Daniel
Formato: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/199857
Acesso em linha:http://hdl.handle.net/10261/199857
Access Level:acceso abierto
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spelling Squaramide‐IRMOF‐16 analogue for catalysis of solvent‐free, epoxide ring‐opening tandem and multicomponent reactionsVignatti, ClaudiaLuis-Barrera, JavierGuillerm, VincentImaz, InharMas-Ballesté, RubénAlemán, JoséMaspoch, DanielTandem and multicomponent one‐pot reactions are highly attractive because they enable synthesis of target molecules in a single reaction vessel. However, they are difficult to control, as they can lead to the formation of many undesired side‐products. Herein we report the use of metal‐organic framework (MOF) pores decorated with organocatalytic squaramide moieties to confine ring‐opening epoxide reactions of diverse substrates. Controlled mono‐addition or tandem reactions inside the pores yield 1,2‐aminoalcohols or 1,2,2′‐aminodialcohols, respectively, in good yields. In addition, this squaramide‐functionalised MOF enables catalysis of higher‐complexity multicomponent reactions such as the catalytic ring‐opening of two different epoxides by a single amine to afford 1,2,2′‐aminodialcohols.This work was supported by the Spanish MINECO (projects PN MAT2015‐65354‐C2‐1‐R and CTQ2015‐64561‐R), the Catalan AGAUR (project 2014 SGR 80), the ERC under the EU FP7 (ERC−Co 615954 and ERC‐CG 647550), and European Union's Horizon 2020 research and innovation programme under grant agreement No 685727. It was also funded by the CERCA Programme/Generalitat de Catalunya. ICN2 acknowledges the support of the Spanish MINECO through the Severo Ochoa Centers of Excellence Program, under Grant SEV‐2013‐0295.Peer reviewedWiley-VCHMinisterio de Economía y Competitividad (España)European Research CouncilGeneralitat de CatalunyaEuropean CommissionConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202020202018info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/199857reponame: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##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2015‐65354‐C2‐1‐Rinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015‐64561‐Rinfo:eu-repo/grantAgreement/EC/FP7/615954info:eu-repo/grantAgreement/EC/FP7/647550info:eu-repo/grantAgreement/EC/H2020/685727info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SEV‐2013‐0295Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1998572026-05-22T06:33:51Z
dc.title.none.fl_str_mv Squaramide‐IRMOF‐16 analogue for catalysis of solvent‐free, epoxide ring‐opening tandem and multicomponent reactions
title Squaramide‐IRMOF‐16 analogue for catalysis of solvent‐free, epoxide ring‐opening tandem and multicomponent reactions
spellingShingle Squaramide‐IRMOF‐16 analogue for catalysis of solvent‐free, epoxide ring‐opening tandem and multicomponent reactions
Vignatti, Claudia
title_short Squaramide‐IRMOF‐16 analogue for catalysis of solvent‐free, epoxide ring‐opening tandem and multicomponent reactions
title_full Squaramide‐IRMOF‐16 analogue for catalysis of solvent‐free, epoxide ring‐opening tandem and multicomponent reactions
title_fullStr Squaramide‐IRMOF‐16 analogue for catalysis of solvent‐free, epoxide ring‐opening tandem and multicomponent reactions
title_full_unstemmed Squaramide‐IRMOF‐16 analogue for catalysis of solvent‐free, epoxide ring‐opening tandem and multicomponent reactions
title_sort Squaramide‐IRMOF‐16 analogue for catalysis of solvent‐free, epoxide ring‐opening tandem and multicomponent reactions
dc.creator.none.fl_str_mv Vignatti, Claudia
Luis-Barrera, Javier
Guillerm, Vincent
Imaz, Inhar
Mas-Ballesté, Rubén
Alemán, José
Maspoch, Daniel
author Vignatti, Claudia
author_facet Vignatti, Claudia
Luis-Barrera, Javier
Guillerm, Vincent
Imaz, Inhar
Mas-Ballesté, Rubén
Alemán, José
Maspoch, Daniel
author_role author
author2 Luis-Barrera, Javier
Guillerm, Vincent
Imaz, Inhar
Mas-Ballesté, Rubén
Alemán, José
Maspoch, Daniel
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
European Research Council
Generalitat de Catalunya
European Commission
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
description Tandem and multicomponent one‐pot reactions are highly attractive because they enable synthesis of target molecules in a single reaction vessel. However, they are difficult to control, as they can lead to the formation of many undesired side‐products. Herein we report the use of metal‐organic framework (MOF) pores decorated with organocatalytic squaramide moieties to confine ring‐opening epoxide reactions of diverse substrates. Controlled mono‐addition or tandem reactions inside the pores yield 1,2‐aminoalcohols or 1,2,2′‐aminodialcohols, respectively, in good yields. In addition, this squaramide‐functionalised MOF enables catalysis of higher‐complexity multicomponent reactions such as the catalytic ring‐opening of two different epoxides by a single amine to afford 1,2,2′‐aminodialcohols.
publishDate 2018
dc.date.none.fl_str_mv 2018
2020
2020
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/10261/199857
url http://hdl.handle.net/10261/199857
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#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2015‐65354‐C2‐1‐R
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015‐64561‐R
info:eu-repo/grantAgreement/EC/FP7/615954
info:eu-repo/grantAgreement/EC/FP7/647550
info:eu-repo/grantAgreement/EC/H2020/685727
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SEV‐2013‐0295
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
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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