Imidazol(in)ium Hydrogen Carbonates as a Genuine Source of N-Heterocyclic Carbenes (NHCs): Applications to the Facile Preparation of NHC Metal Complexes and to NHC-Organocatalyzed Molecular and Macromolecular Syntheses
| dc.rights.license | open | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| dc.contributor.author | FÈVRE, Maréva | |
| 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] | |
| dc.contributor.author | LETENEUR, Alexandre | |
| 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 | VIGNOLLE, Joan | |
| hal.structure.identifier | Laboratoire de Chimie des Polymères Organiques [LCPO] | |
| hal.structure.identifier | Team 1 LCPO : Polymerization Catalyses & Engineering | |
| dc.contributor.author | TATON, Daniel | |
| hal.structure.identifier | Laboratoire de Chimie théorique et Physico-chimie moléculaire [LCTPCM] | |
| dc.contributor.author | MIQUEU, Karinne | |
| hal.structure.identifier | Laboratoire de Chimie théorique et Physico-chimie moléculaire [LCTPCM] | |
| dc.contributor.author | SOTIROPOULOS, Jean-Marc | |
| dc.date.accessioned | 2020 | |
| dc.date.available | 2020 | |
| dc.date.issued | 2012 | |
| dc.identifier.issn | 0002-7863 | |
| dc.identifier.uri | https://oskar-bordeaux.fr/handle/20.500.12278/20487 | |
| dc.description.abstractEn | Anion metathesis of imidazol(in)ium chlorides with KHCO3 afforded an easy one step access to air stable imidazol(in)ium hydrogen carbonates, denoted as [NHC(H)][HCO3]. In solution, these compounds were found to be in equilibrium with their corresponding imidazol(in)ium carboxylates, referred to as N-heterocyclic carbene (NHC)-CO2 adducts. The [NHC(H)][HCO3] salts were next shown to behave as masked NHCs, allowing for the NHC moiety to be readily transferred to both organic and organometallic substrates, without the need for dry and oxygen-free conditions. In addition, such [NHC(H)][HCO3] precursors were successfully investigated as precatalysts in two selected organocatalyzed reactions of molecular chemistry and polymer synthesis, namely, the benzoin condensation reaction and the ring-opening polymerization of D,L-lactide, respectively. The generation of NHCs from [NHC(H)][HCO3] precursors occurred via the formal loss of H2CO3 via a concerted low energy pathway, as substantiated by Density Functional Theory (DFT) calculations. | |
| dc.language.iso | en | |
| dc.publisher | American Chemical Society | |
| dc.subject.en | TRANSFER AGENTS | |
| dc.subject.en | LIGAND PRECURSORS | |
| dc.subject.en | LIVING POLYMERIZATION | |
| dc.subject.en | ORGANOMETALLIC CATALYSIS | |
| dc.subject.en | IMIDAZOLIUM CARBOXYLATES | |
| dc.subject.en | OLEFIN METATHESIS | |
| dc.subject.en | METATHESIS CATALYSTS | |
| dc.subject.en | RING-OPENING POLYMERIZATION | |
| dc.subject.en | IONIC LIQUIDS | |
| dc.subject.en | STRUCTURAL-CHARACTERIZATION | |
| dc.title.en | Imidazol(in)ium Hydrogen Carbonates as a Genuine Source of N-Heterocyclic Carbenes (NHCs): Applications to the Facile Preparation of NHC Metal Complexes and to NHC-Organocatalyzed Molecular and Macromolecular Syntheses | |
| dc.type | Article de revue | |
| dc.identifier.doi | 10.1021/ja3005804 | |
| dc.subject.hal | Chimie/Polymères | |
| bordeaux.journal | Journal of the American Chemical Society | |
| bordeaux.page | 6776-6784 | |
| bordeaux.volume | 134 | |
| bordeaux.hal.laboratories | Laboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629 | * |
| bordeaux.issue | 15 | |
| bordeaux.institution | Bordeaux INP | |
| bordeaux.institution | Université de Bordeaux | |
| bordeaux.peerReviewed | oui | |
| hal.identifier | hal-00744334 | |
| hal.version | 1 | |
| hal.origin.link | https://hal.archives-ouvertes.fr//hal-00744334v1 | |
| bordeaux.COinS | ctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.date=2012&rft.volume=134&rft.issue=15&rft.spage=6776-6784&rft.epage=6776-6784&rft.eissn=0002-7863&rft.issn=0002-7863&rft.au=F%C3%88VRE,%20Mar%C3%A9va&PINAUD,%20Julien&LETENEUR,%20Alexandre&GNANOU,%20Yves&VIGNOLLE,%20Joan&rft.genre=article |
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