Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes

Various cavitand based polyphenols were prepared from cheap and accessible aldehyde and resorcinol/pyrogallol reagents giving their respective resorcin[4]- or pyrogallol[4]arenes. The pre- organization of the phenolic units allows for intra- and intermolecular hydrogen bond (HB) networks affecting b...

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Autores: Martínez-Rodríguez, Luis, Otalora Garmilla, Javier, Kleij, Arjan W.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2016
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:2072/356176
Acceso en línea:http://hdl.handle.net/2072/356176
https://doi.org/10.1002/cssc.201501463
Access Level:acceso abierto
Palabra clave:54
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spelling Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and OxiranesMartínez-Rodríguez, LuisOtalora Garmilla, JavierKleij, Arjan W.54Various cavitand based polyphenols were prepared from cheap and accessible aldehyde and resorcinol/pyrogallol reagents giving their respective resorcin[4]- or pyrogallol[4]arenes. The pre- organization of the phenolic units allows for intra- and intermolecular hydrogen bond (HB) networks affecting both the reactivity and stability of these HB donor catalysts. Unexpectedly, we found that resorcin[4]arenes show cooperative catalysis behavior compared to parent resorcinol in the catalytic coupling of epoxides and CO2 with significantly higher turnover. At elevated reaction temperatures, the resorcin[4]arene based catalyst 3d displays the best catalytic performance with both very high turnover numbers and frequencies combining increased reactivity and stability compared to pyrogallol, and ample substrate scope. This type of polyphenol structure thus illustrates the importance of a new, highly competitive organocatalyst design for devising sustainable CO2 conversion processes.2016info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersion749 p.application/pdfhttp://hdl.handle.net/2072/356176https://doi.org/10.1002/cssc.201501463RECERCAT (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:2072/3561762026-05-29T05:05:01Z
dc.title.none.fl_str_mv Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes
title Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes
spellingShingle Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes
Martínez-Rodríguez, Luis
54
title_short Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes
title_full Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes
title_fullStr Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes
title_full_unstemmed Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes
title_sort Cavitand based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes
dc.creator.none.fl_str_mv Martínez-Rodríguez, Luis
Otalora Garmilla, Javier
Kleij, Arjan W.
author Martínez-Rodríguez, Luis
author_facet Martínez-Rodríguez, Luis
Otalora Garmilla, Javier
Kleij, Arjan W.
author_role author
author2 Otalora Garmilla, Javier
Kleij, Arjan W.
author2_role author
author
dc.subject.none.fl_str_mv 54
topic 54
description Various cavitand based polyphenols were prepared from cheap and accessible aldehyde and resorcinol/pyrogallol reagents giving their respective resorcin[4]- or pyrogallol[4]arenes. The pre- organization of the phenolic units allows for intra- and intermolecular hydrogen bond (HB) networks affecting both the reactivity and stability of these HB donor catalysts. Unexpectedly, we found that resorcin[4]arenes show cooperative catalysis behavior compared to parent resorcinol in the catalytic coupling of epoxides and CO2 with significantly higher turnover. At elevated reaction temperatures, the resorcin[4]arene based catalyst 3d displays the best catalytic performance with both very high turnover numbers and frequencies combining increased reactivity and stability compared to pyrogallol, and ample substrate scope. This type of polyphenol structure thus illustrates the importance of a new, highly competitive organocatalyst design for devising sustainable CO2 conversion processes.
publishDate 2016
dc.date.none.fl_str_mv 2016
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/2072/356176
https://doi.org/10.1002/cssc.201501463
url http://hdl.handle.net/2072/356176
https://doi.org/10.1002/cssc.201501463
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 749 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
repository.name.fl_str_mv
repository.mail.fl_str_mv
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