Highly Efficient Rh-catalysts Immobilised by π-π Stacking for the Asymmetric Hydroformylation of Norbornene under Continuous Flow Conditions

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dc.contributor.authorCunillera, Anton
dc.contributor.authorBlanco, Carolina
dc.contributor.authorGual, Aitor
dc.contributor.authorMarinkovic, Jakob Maximilian
dc.contributor.authorGarcia-Suarez, Eduardo J.
dc.contributor.authorRiisager, Anders
dc.contributor.authorClaver, Carmen
dc.contributor.authorRuiz, Aurora
dc.contributor.authorGodard, Cyril
dc.contributor.institutionTecnalia Research & Innovation
dc.date.accessioned2024-07-24T12:02:57Z
dc.date.available2024-07-24T12:02:57Z
dc.date.issued2019-04-18
dc.descriptionPublisher Copyright: © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.description.abstractThe application of C1-symmetrical diphosphite ligands containing furanose backbone in the Rh-catalysed asymmetric hydroformylation of norbornene is described. The catalysts were highly active and produced exclusively exo-norbornanecarboxaldehyde with enantioselectivities (ee) up to 71 %. Considering these promising results, the ligands were modified with a pyrene moiety to accomplish their immobilisation onto carbon materials. The corresponding Rh complexes bearing the novel pyrene-tagged ligands were synthesised and immobilised onto multiwalled carbon nanotubes (MWCNT), reduced graphene oxide (rGO) and carbon beads (CBs). The novel catalytic systems were tested in the asymmetric hydroformylation of norbornene providing similar performance in terms of both activity and selectivity compared to the non-immobilised systems. The recyclability of the new heterogenised catalysts was studied in the target reaction in batch mode. Nevertheless, the recycling was unsuccessful due to catalyst leaching. When used under continuous flow mode, these catalysts revealed robust and provided even higher ee than the corresponding homogeneous systems.en
dc.description.sponsorshipThe authors are grateful to the Ministerio de Economia y Competividad and the Fondo Europeo de Desarrollo Regional FEDER (CTQ2016-75016-R, AEI/FEDER,UE) for funding and PhD grant (BES-2014-069199) to AC. The authors also gratefully acknowledge financial support from the European Commission within the Horizon2020-SPIRE project ROMEO (grant agreement number 680395). TheauthorsaregratefultotheMinisteriodeEconomiay CompetividadandtheFondoEuropeodeDesarrolloRegional FEDER(CTQ2016-75016-R,AEI/FEDER,UE)forfundingandPhD grant(BES-2014-069199)toAC.Theauthorsalsogratefully acknowledgefinancialsupportfromtheEuropeanCommission withintheHorizon2020-SPIREprojectROMEO(grantagreement number680395).
dc.description.statusPeer reviewed
dc.format.extent11
dc.identifier.citationCunillera , A , Blanco , C , Gual , A , Marinkovic , J M , Garcia-Suarez , E J , Riisager , A , Claver , C , Ruiz , A & Godard , C 2019 , ' Highly Efficient Rh-catalysts Immobilised by π-π Stacking for the Asymmetric Hydroformylation of Norbornene under Continuous Flow Conditions ' , ChemCatChem , vol. 11 , no. 8 , pp. 2195-2205 . https://doi.org/10.1002/cctc.201900211
dc.identifier.doi10.1002/cctc.201900211
dc.identifier.issn1867-3880
dc.identifier.urihttps://hdl.handle.net/11556/3300
dc.identifier.urlhttp://www.scopus.com/inward/record.url?scp=85063800651&partnerID=8YFLogxK
dc.language.isoeng
dc.relation.ispartofChemCatChem
dc.relation.projectIDAEI/FEDER, BES-2014-069199
dc.relation.projectIDFondo Europeo de Desarrollo Regional FEDER
dc.relation.projectIDMinisterio de Economia y Competividad
dc.relation.projectIDEuropean Commission, EU, 680395
dc.relation.projectIDEuropean Regional Development Fund, FEDER, CTQ2016-75016-R
dc.relation.projectIDUniversity of the East, UE
dc.rightsinfo:eu-repo/semantics/restrictedAccess
dc.subject.keywordscontinuous flow
dc.subject.keywordsdiphosphites
dc.subject.keywordsenantioselective hydroformylation
dc.subject.keywordssupported Rh catalysts.
dc.subject.keywordsπ interactions
dc.subject.keywordsCatalysis
dc.subject.keywordsPhysical and Theoretical Chemistry
dc.subject.keywordsOrganic Chemistry
dc.subject.keywordsInorganic Chemistry
dc.titleHighly Efficient Rh-catalysts Immobilised by π-π Stacking for the Asymmetric Hydroformylation of Norbornene under Continuous Flow Conditionsen
dc.typejournal article
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