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N-Heterocyclic carbenes (NHCs) as organocatalysts and structural components in metal-free polymer synthesis

dc.rights.licenseopen
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorFÈVRE, Maréva
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorPINAUD, Julien
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorGNANOU, Yves
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]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorTATON, Daniel
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2013
dc.identifier.issn0306-0012
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20390
dc.description.abstractEnThe chemistry of N-heterocyclic carbenes (NHCs) has witnessed tremendous development in the past two decades: NHCs have not only become versatile ligands for transition metals, but have also emerged as powerful organic catalysts in molecular chemistry and, more recently, in metal-free polymer synthesis. To understand the success of NHCs, this review first presents the electronic properties of NHCs, their main synthetic methods, their handling, and their reactivity. Their ability to activate key functional groups (e.g. aldehydes, esters, heterocycles, silyl ketene acetals, alcohols) is then discussed in the context of molecular chemistry. Focus has been placed on the activation of substrates finding analogies with monomers (e.g. bis-aldehydes, multi-isocyanates, cyclic esters, epoxides, N-carboxyanhydrides, etc.) and/or initiators (e.g. hydroxy- or trimethylsilyl-containing reagents) employed in such "organopolymerisation" reactions utilizing NHCs. A variety of metal-free polymers, including aliphatic polyesters and polyethers, poly(alpha-peptoid)s, poly(meth)acrylates, polyurethanes, or polysiloxanes can be obtained in this way. The last section covers the use of NHCs as structural components of the polymer chain. Indeed, NHC-based photoinitiators, chain transfer agents or functionalizing agents, as well as bifunctional NHC monomer substrates, can also serve for metal-free polymer synthesis.
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.subject.enCYCLIC ESTERS
dc.subject.enBLOCK-COPOLYMERS
dc.subject.enRING-OPENING POLYMERIZATION
dc.subject.enCROSS-COUPLING REACTIONS
dc.subject.enMEDIATED ZWITTERIONIC POLYMERIZATION
dc.subject.enCHAIN ORGANOMETALLIC POLYMERS
dc.subject.enL-MALIC ACID
dc.subject.enLIVING POLYMERIZATION
dc.subject.enNUCLEOPHILIC CARBENES
dc.subject.enCATALYTIC-ACTIVITY
dc.title.enN-Heterocyclic carbenes (NHCs) as organocatalysts and structural components in metal-free polymer synthesis
dc.typeArticle de revue
dc.identifier.doi10.1039/c2cs35383k
dc.subject.halChimie/Polymères
bordeaux.journalChemical Society Reviews
bordeaux.page2142-2172
bordeaux.volume42
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue5
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-00932343
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-00932343v1
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