Mostrar el registro sencillo del ítem

Poly(ionic liquid)s Based on Imidazolium Hydrogen Carbonate Monomer Units as Recyclable Polymer-Supported N-Heterocyclic Carbenes: Use in Organocatalysis

dc.rights.licenseopen
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorCOUPILLAUD, Paul
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorPINAUD, Julien
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorGUIDOLIN, Nicolas
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorVIGNOLLE, Joan
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorFÈVRE, Maréva
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorVEAUDECRENNE, Ellen
hal.structure.identifierUniv Basque Country POLYMAT
dc.contributor.authorMECERREYES, David
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorTATON, Daniel
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2013
dc.identifier.issn0887-624X
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20392
dc.description.abstractEnSynthesis of novel poly(ionic liquid)s, namely, poly(1-vinyl-3-alkylimidazolium hydrogen carbonate)s, denoted as poly([NHC(H)][HCO3])s or PVRImHCO(3), where R is an alkyl group (R=ethyl, butyl, phenylethyl, dodecyl), is described. Two distinct synthetic routes were explored. The first method is based on the free-radical polymerization (FRP) of 1-vinyl-3-alkylimidazolium monomers featuring a hydrogen carbonate counter anion (HCO3-), denoted as VRImHCO(3). The latter monomers were readily synthesized by alkylation of 1-vinylimidazole (VIm), followed by direct anion exchange of 1-vinyl-3-alkylimidazolium bromide monomers (VRImBr), using potassium hydrogen carbonate (KHCO3) in methanol at room temperature. Alternatively, the same anion exchange method could be applied onto FRP-derived poly(1-vinyl-3-alkylimidazolium bromide) precursors (PVRImBr). All PVRImHCO(3) salts proved air stable and could be manipulated without any particular precautions. They could serve as polymer-supported precatalysts to generate polymer-supported N-heterocyclic carbenes, referred to as poly(NHC)s, formally by a loss of H2CO3 (H2O +CO2) in solution. This was demonstrated through selected organocatalyzed reactions of molecular chemistry, known as being efficiently mediated by molecular NHC catalysts, including benzoin condensation, transesterification and cyanosilylation of aldehyde. Of particular interest, recycling of the polymer-supported precatalysts was possible by re-carboxylation of in situ generated poly(NHC)s. Organocatalyzed reactions could be performed with excellent yields, even after five catalytic cycles.
dc.language.isoen
dc.publisherWiley
dc.subject.ensynthesis
dc.subject.encatalysis
dc.subject.enN-heterocyclic carbenes
dc.subject.enorganocatalysis
dc.subject.enpoly(ionic liquid)s
dc.subject.enpolymer-supported catalysts
dc.subject.enradical polymerization
dc.title.enPoly(ionic liquid)s Based on Imidazolium Hydrogen Carbonate Monomer Units as Recyclable Polymer-Supported N-Heterocyclic Carbenes: Use in Organocatalysis
dc.typeArticle de revue
dc.identifier.doi10.1002/pola.26869
dc.subject.halChimie/Polymères
bordeaux.journalJournal of Polymer Science Part A: Polymer Chemistry
bordeaux.page4530-4540
bordeaux.volume51
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue21
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-00931021
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-00931021v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Journal%20of%20Polymer%20Science%20Part%20A:%20Polymer%20Chemistry&rft.date=2013&rft.volume=51&rft.issue=21&rft.spage=4530-4540&rft.epage=4530-4540&rft.eissn=0887-624X&rft.issn=0887-624X&rft.au=COUPILLAUD,%20Paul&PINAUD,%20Julien&GUIDOLIN,%20Nicolas&VIGNOLLE,%20Joan&F%C3%88VRE,%20Mar%C3%A9va&rft.genre=article


Archivos en el ítem

ArchivosTamañoFormatoVer

No hay archivos asociados a este ítem.

Este ítem aparece en la(s) siguiente(s) colección(ones)

Mostrar el registro sencillo del ítem