Pushing the Limits with Squaramide-Based Organocatalysts in Cyclic Carbonate Synthesis

Squaramides are presented as highly modular, easy to optimize and highly efficient catalysts for the conversion of epoxides and carbon dioxide into cyclic organic carbonates (COCs). The catalytic potential of these squaramides, in combination with a suitable halide nucleophile, is particularly noted...

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Autores: Sopeña, Sergio, Martin, Eddy, Escudero-Adán, Eduardo C., Kleij, Arjan W.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución: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:2072/356048
Acceso en línea:http://hdl.handle.net/2072/356048
https://doi.org/10.1021/acscatal.7b00475
Access Level:acceso abierto
Palabra clave:54
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spelling Pushing the Limits with Squaramide-Based Organocatalysts in Cyclic Carbonate SynthesisSopeña, SergioMartin, EddyEscudero-Adán, Eduardo C.Kleij, Arjan W.54Squaramides are presented as highly modular, easy to optimize and highly efficient catalysts for the conversion of epoxides and carbon dioxide into cyclic organic carbonates (COCs). The catalytic potential of these squaramides, in combination with a suitable halide nucleophile, is particularly noted when internal epoxides are examined as substrates and their transformation into disubstituted COCs marks a rare case of an effective organocatalyst for these challenging conversions. Control experiments support the mechanistic view that the squaramides are predominantly involved in the stabilization of intermediate oxo- and carbonato-anions which, after their formation, are able to displace a bromide nucleophile from an initially formed 1:1 assembly comprising the squaramide host.2017info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion3532 p.application/pdfhttp://hdl.handle.net/2072/356048https://doi.org/10.1021/acscatal.7b00475RECERCAT (Dipòsit de la Recerca de Catalunya)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésL'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons:http://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:2072/3560482026-05-29T05:05:01Z
dc.title.none.fl_str_mv Pushing the Limits with Squaramide-Based Organocatalysts in Cyclic Carbonate Synthesis
title Pushing the Limits with Squaramide-Based Organocatalysts in Cyclic Carbonate Synthesis
spellingShingle Pushing the Limits with Squaramide-Based Organocatalysts in Cyclic Carbonate Synthesis
Sopeña, Sergio
54
title_short Pushing the Limits with Squaramide-Based Organocatalysts in Cyclic Carbonate Synthesis
title_full Pushing the Limits with Squaramide-Based Organocatalysts in Cyclic Carbonate Synthesis
title_fullStr Pushing the Limits with Squaramide-Based Organocatalysts in Cyclic Carbonate Synthesis
title_full_unstemmed Pushing the Limits with Squaramide-Based Organocatalysts in Cyclic Carbonate Synthesis
title_sort Pushing the Limits with Squaramide-Based Organocatalysts in Cyclic Carbonate Synthesis
dc.creator.none.fl_str_mv Sopeña, Sergio
Martin, Eddy
Escudero-Adán, Eduardo C.
Kleij, Arjan W.
author Sopeña, Sergio
author_facet Sopeña, Sergio
Martin, Eddy
Escudero-Adán, Eduardo C.
Kleij, Arjan W.
author_role author
author2 Martin, Eddy
Escudero-Adán, Eduardo C.
Kleij, Arjan W.
author2_role author
author
author
dc.subject.none.fl_str_mv 54
topic 54
description Squaramides are presented as highly modular, easy to optimize and highly efficient catalysts for the conversion of epoxides and carbon dioxide into cyclic organic carbonates (COCs). The catalytic potential of these squaramides, in combination with a suitable halide nucleophile, is particularly noted when internal epoxides are examined as substrates and their transformation into disubstituted COCs marks a rare case of an effective organocatalyst for these challenging conversions. Control experiments support the mechanistic view that the squaramides are predominantly involved in the stabilization of intermediate oxo- and carbonato-anions which, after their formation, are able to displace a bromide nucleophile from an initially formed 1:1 assembly comprising the squaramide host.
publishDate 2017
dc.date.none.fl_str_mv 2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/2072/356048
https://doi.org/10.1021/acscatal.7b00475
url http://hdl.handle.net/2072/356048
https://doi.org/10.1021/acscatal.7b00475
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 3532 p.
application/pdf
dc.source.none.fl_str_mv RECERCAT (Dipòsit de la Recerca de Catalunya)
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
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repository.mail.fl_str_mv
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