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Sunlight-Driven Copper-Catalyst Activation Applied to Photolatent Click Chemistry

hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorBENIAZZA, Rédouane
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorLAMBERT, Romain
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorHARMAND, Lydie
hal.structure.identifierDépartement de Chimie Moléculaire - Chimie Inorganique Redox [DCM - CIRE]
dc.contributor.authorMOLTON, Florian
hal.structure.identifierDépartement de Chimie Moléculaire - Chimie Inorganique Redox [DCM - CIRE]
dc.contributor.authorDUBOC, Carole
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
hal.structure.identifierLaboratoire Ondes et Matière d'Aquitaine [LOMA]
dc.contributor.authorDENISOV, Sergey
hal.structure.identifierLaboratoire Ondes et Matière d'Aquitaine [LOMA]
dc.contributor.authorJONUSAUSKAS, Gediminas
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorMCCLENAGHAN, Nathan D
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorLASTÉCOUÈRES, Dominique
hal.structure.identifierInstitut des Sciences Moléculaires [ISM]
dc.contributor.authorVINCENT, Jean-Marc
dc.date.created2014-06-20
dc.date.issued2014
dc.identifier.issn0947-6539
dc.description.abstractEnThe synthesis, full characterization, photoreduction properties, and catalytic activity for the copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) reaction of a copper(II)-DMEDA (N,N′-dimethylethylendiamine) complex is reported. Spectroscopic studies (UV/Vis, EPR) demonstrated that under daylight illumination highly effective copper(II) to copper(I) reduction occurs in this complex. These findings are in agreement with a high photoreduction quantum yield value of 0.22 in MeOH, and a value approaching unity as determined in THF. The reduction process, which can also be conducted by irradiation at 365 nm by using a standard TLC (thin layer chromatography) lamp, is ascribed to a highly efficient photoinduced electron transfer (PET) process mediated by the benzophenone photosensitizer present in the carboxylate counterion. Having deaerated the reaction mixture, the photogenerated copper(I) species proved to be highly active for the CuAAC reaction, demonstrated by reactions conducted with low catalyst loading (0.5 mol %) on a range of clickable protected and non-protected mono- and disaccharides. Once initiated, the reaction can be stopped at any time on introducing air into the reaction medium. Deoxygenation followed by irradiation restores the activity, making the copper(II)-DMEDA complex a switchable catalyst of practical value.
dc.description.sponsorshipActivation de catalyseurs par transfert d'électron photoinduit - ANR-13-BS07-0006
dc.language.isoen
dc.publisherWiley-VCH Verlag
dc.rights.urihttp://creativecommons.org/licenses/by-sa/
dc.subject.enbenzophenone
dc.subject.enclick chemistry
dc.subject.encopper catalysts
dc.subject.enphotoactivation
dc.subject.enphotoinduced electron transfer
dc.title.enSunlight-Driven Copper-Catalyst Activation Applied to Photolatent Click Chemistry
dc.typeArticle de revue
dc.identifier.doi10.1002/chem.201404056
dc.subject.halChimie/Catalyse
dc.subject.halChimie/Chimie organique
dc.description.sponsorshipEuropeCommunication between Functional Molecules using Photocontrolled Ions
bordeaux.journalChemistry - A European Journal
bordeaux.page13181-13187
bordeaux.volume20
bordeaux.issue41
bordeaux.peerReviewedoui
hal.identifierhal-01071826
hal.version1
hal.popularnon
hal.audienceInternationale
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-01071826v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Chemistry%20-%20A%20European%20Journal&rft.date=2014&rft.volume=20&rft.issue=41&rft.spage=13181-13187&rft.epage=13181-13187&rft.eissn=0947-6539&rft.issn=0947-6539&rft.au=BENIAZZA,%20R%C3%A9douane&LAMBERT,%20Romain&HARMAND,%20Lydie&MOLTON,%20Florian&DUBOC,%20Carole&rft.genre=article


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