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Azaphosphatranes as Hydrogen-Bonding Organocatalysts for the Activation of Carbonyl Groups: Investigation of Lactide Ring-Opening Polymerization

dc.rights.licenseopen
hal.structure.identifierLaboratoire de Chimie - UMR5182 [LC]
hal.structure.identifierDepartment of Chemistry, East China Normal University, Shanghai [ECNU]
dc.contributor.authorZHANG, Dawei
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorJARDEL, Damien
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorPERUCH, Frédéric
IDREF: 152900748
hal.structure.identifierLaboratoire de Chimie - UMR5182 [LC]
dc.contributor.authorCALIN, Nathalie
hal.structure.identifierLaboratoire de Chimie, Catalyse, Polymères et Procédés, R 5265 [C2P2]
dc.contributor.authorDUFAUD, Véronique
hal.structure.identifierLaboratoire de Chimie - UMR5182 [LC]
dc.contributor.authorDUTASTA, Jean-Pierre
hal.structure.identifierLaboratoire de Chimie - UMR5182 [LC]
hal.structure.identifierInstitut des Sciences Moléculaires de Marseille [ISM2]
dc.contributor.authorMARTINEZ, Alexandre
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorBIBAL, Brigitte
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2016
dc.identifier.issn1434-193X
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20178
dc.description.abstractEnThe hydrogen-bonding activation of C=O bonds by azaphosphatranes was explored in a model reaction, i. e., the ring-opening polymerization of lactide. The polymerization process was controlled, and allowed the preparation of polylactides with narrow dispersity under mild conditions (20 degrees C, 24 h, 10 mol-% catalyst loading). Interestingly, the steric hindrance of azaphosphatranes, as globular rigid structures, prevents any undesired interaction with the tertiary amine cocatalysts, as shown by X-ray analysis and semi-empirical calculations. In contrast to their organocatalytic activity in the CO2/epoxide reaction, all of the phosphonium derivatives tested were found to be efficient catalysts in this ROP benchmark reaction.
dc.language.isoen
dc.publisherWiley-VCH Verlag
dc.subject.enPhosphorus
dc.subject.enHydrogen bonds
dc.subject.enOrganocatalysis
dc.subject.enRing-opening polymerization
dc.subject.enLactide
dc.subject.enASYMMETRIC CATALYSIS
dc.subject.enLIVING POLYMERIZATION
dc.subject.enORGANIC-SYNTHESIS
dc.subject.enCYCLIC ESTERS
dc.subject.enPROAZAPHOSPHATRANES
dc.subject.enBASE
dc.subject.enCO2
dc.subject.enCONVERSION
dc.subject.enDONORS
dc.title.enAzaphosphatranes as Hydrogen-Bonding Organocatalysts for the Activation of Carbonyl Groups: Investigation of Lactide Ring-Opening Polymerization
dc.typeArticle de revue
dc.identifier.doi10.1002/ejoc.201600080
dc.subject.halChimie/Polymères
bordeaux.journalEuropean Journal of Organic Chemistry
bordeaux.page1619-1624
bordeaux.volume8
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-01383093
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-01383093v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=European%20Journal%20of%20Organic%20Chemistry&rft.date=2016&rft.volume=8&rft.spage=1619-1624&rft.epage=1619-1624&rft.eissn=1434-193X&rft.issn=1434-193X&rft.au=ZHANG,%20Dawei&JARDEL,%20Damien&PERUCH,%20Fr%C3%A9d%C3%A9ric&CALIN,%20Nathalie&DUFAUD,%20V%C3%A9ronique&rft.genre=article


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