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Poly(N-heterocyclic-carbene)s and their CO(2) Adducts as Recyclable Polymer-Supported Organocatalysts for Benzoin Condensation and Transesterification Reactions
| dc.rights.license | open | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| dc.contributor.author | PINAUD, Julien | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Team 1 LCPO : Polymerization Catalyses & Engineering | |
| dc.contributor.author | VIGNOLLE, Joan | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| dc.contributor.author | GNANOU, Yves | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Team 1 LCPO : Polymerization Catalyses & Engineering | |
| dc.contributor.author | TATON, Daniel | |
| dc.date.accessioned | 2020 | |
| dc.date.available | 2020 | |
| dc.date.created | 2011 | |
| dc.date.issued | 2011 | |
| dc.identifier.issn | 0024-9297 | |
| dc.identifier.uri | https://oskar-bordeaux.fr/handle/20.500.12278/20542 | |
| dc.description.abstractEn | The synthesis of poly(N-heterocyclic carbene)s, denoted poly-(NHC)s, and of their poly(NHC-CO(2)) adducts for a use in organocatalysis is described. Poly(NHC)s were readily obtained in a three-step sequence of reactions, involving i) the free-radical polymerization of ionic liquid monomers, that is, 1-vinyl-3-alkylimidazolium-type monomers with bromide (Br(-)) as counteranion, followed by ii) anion exchange of Br(-) for bis(trifluoromethanesulfonyl)imide ((-)NTf2), of the poly(1-vinyl-3-alkylimidazolium bromide) precursors, affording poly(1-vinyl-3-alkylimidazolium bis(trifluorornethanesulfonyl)imide) derivatives, and iii) deprotonation of the latter polymeric ionic liquids with a strong base. Carbon dioxide (CO(2)) was found to reversibly react with poly(NHC)s forming relatively air-stable and thermolabile poly(NHC-CO(2)) adducts. Both poly(NHC)s and their poly(NHC-CO(2)) adducts were used as polymer-supported organic catalysts and precatalysts, respectively, in transesterification and benzoin condensation reactions under homogeneous conditions. Both types of polymer-supported NHCs were recycled and used several times, but the manipulation of poly(NHC)s like their molecular NHC analogues-was more complicated owing to their air and moisture sensitivity. In this regard, zwitterionic poly(NHC-CO(2)) adducts like their molecular NHC-CO(2) analogues could be easier manipulated than their bare poly(NHC) counterparts, providing good to excellent yields even after several organocatalytic cycles, in particular toward the transesterification reaction. | |
| dc.language.iso | en | |
| dc.publisher | American Chemical Society | |
| dc.subject.en | N-HETEROCYCLIC CARBENES | |
| dc.subject.en | RING-OPENING POLYMERIZATION | |
| dc.subject.en | IONIC LIQUIDS | |
| dc.subject.en | BLOCK-COPOLYMERS | |
| dc.subject.en | CATALYTIC-ACTIVITY | |
| dc.subject.en | ORGANOMETALLIC CATALYSIS | |
| dc.subject.en | POLY(ETHYLENE OXIDE)S | |
| dc.subject.en | LIVING POLYMERIZATION | |
| dc.subject.en | PYRIDINE OLIGOMERS | |
| dc.subject.en | OLEFIN METATHESIS | |
| dc.title.en | Poly(N-heterocyclic-carbene)s and their CO(2) Adducts as Recyclable Polymer-Supported Organocatalysts for Benzoin Condensation and Transesterification Reactions | |
| dc.type | Article de revue | |
| dc.identifier.doi | 10.1021/ma1024285 | |
| dc.subject.hal | Chimie/Polymères | |
| bordeaux.journal | Macromolecules | |
| bordeaux.page | 1900-1908 | |
| bordeaux.volume | 44 | |
| bordeaux.hal.laboratories | Laboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629 | * |
| bordeaux.issue | 7 | |
| bordeaux.institution | Bordeaux INP | |
| bordeaux.institution | Université de Bordeaux | |
| bordeaux.peerReviewed | oui | |
| hal.identifier | hal-00677776 | |
| hal.version | 1 | |
| hal.origin.link | https://hal.archives-ouvertes.fr//hal-00677776v1 | |
| bordeaux.COinS | ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Macromolecules&rft.date=2011&rft.volume=44&rft.issue=7&rft.spage=1900-1908&rft.epage=1900-1908&rft.eissn=0024-9297&rft.issn=0024-9297&rft.au=PINAUD,%20Julien&VIGNOLLE,%20Joan&GNANOU,%20Yves&TATON,%20Daniel&rft.genre=article |
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