Primary amine-thiourea grafted graphene-based heterogeneous chiral catalysts for highly enantioselective Michael additions

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dc.contributor.authorBadr, Sayed Mustafa
dc.contributor.authorAzlouk, Manel
dc.contributor.authorZor, Erhan
dc.contributor.authorBingol, Haluk
dc.contributor.authorDurmaz, Mustafa
dc.date.accessioned2024-02-23T14:13:09Z
dc.date.available2024-02-23T14:13:09Z
dc.date.issued2022
dc.departmentNEÜen_US
dc.description.abstractHeterogeneous asymmetric catalysis based on earth-abundant carbon materials put together the advantages for the ease of separation, simple regeneration, and high stability of solid catalysts as well as acts as low-cost, environmentally friendly metal-free alternative to the metal-based catalysts. Two new bifunctional carbocatalysts [(S,S) and (R,R) GO-PATU] were prepared by anchoring enantiomerically pure organosilanes bearing primary amine and thiourea groups to the graphene oxide (GO) skeleton covalently via silane coupling reaction. The surface modification of GO was analyzed by a combination of Fourier-transform infrared spectroscopy (FTIR), Raman spectroscopy, X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM) and transmission electron spectroscopy (TEM) techniques. The catalytic performances of graphene-based materials were investigated in the asymmetric Michael addition reactions of alpha,alpha-disubstituted-aldehydes to nitrostyrenes and N-substituted-maleimides. The effects of solvents and Bronsted basic or acidic additives were evaluated using both catalysts and good yields (up to 85%) and stereoselectivities (up to 95% ee) were obtained in dichloromethane at room temperature in the presence of L- and D-camphorsulfonic acid. Besides, recycling and reusing studies of the catalysts were successfully performed.en_US
dc.description.sponsorshipScientific and Technological Research Council of Turkey [T?BI?TAK-117Z406]en_US
dc.description.sponsorshipAcknowledgments The authors are grateful to the Scientific and Technological Research Council of Turkey (T?BI?TAK-117Z406) for the financial support.en_US
dc.identifier.doi10.1016/j.mcat.2022.112383
dc.identifier.issn2468-8231
dc.identifier.scopus2-s2.0-85131046411en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1016/j.mcat.2022.112383
dc.identifier.urihttps://hdl.handle.net/20.500.12452/12330
dc.identifier.volume526en_US
dc.identifier.wosWOS:000809931400003en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofMolecular Catalysisen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectMetal-Free Asymmetric Catalysisen_US
dc.subjectHeterogeneous Catalysten_US
dc.subjectBifunctional Carbocatalysten_US
dc.subjectGraphene Oxideen_US
dc.subjectAsymmetric Michael Additionen_US
dc.titlePrimary amine-thiourea grafted graphene-based heterogeneous chiral catalysts for highly enantioselective Michael additionsen_US
dc.typeArticleen_US

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