N-Heterocyclic carbene-palladium-PEPPSI complexes and their catalytic activity in the direct C-H bond activation of heteroarene derivatives with aryl bromides: synthesis, and antimicrobial and antioxidant activities

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dc.authoridGurbuz, Nevin/0000-0003-3201-3597
dc.authoridMansour, Lamjed/0000-0002-9415-9383
dc.authorwosidGurbuz, Nevin/A-3069-2016
dc.authorwosidMansour, Lamjed/U-3028-2017
dc.contributor.authorHamdi, N.
dc.contributor.authorSlimani, I.
dc.contributor.authorMansour, L.
dc.contributor.authorAlresheedi, Faisal
dc.contributor.authorGurbuz, N.
dc.contributor.authorOzdemir, I.
dc.date.accessioned2024-08-04T20:50:53Z
dc.date.available2024-08-04T20:50:53Z
dc.date.issued2021
dc.departmentİnönü Üniversitesien_US
dc.description.abstractIn this study, a series of unsymmetrical 1,3-disubstituted benzimidazolium chlorides 2a-g with two nitrogen atoms substituted by different alkyl groups were synthesized in high yields as N-heterocyclic carbene (NHC) precursors. These benzimidazolium salts were then converted into the corresponding Pd-NHC complexes of the PEPPSI family (PEPPSI = pyridine-enhanced precatalyst preparation, stabilization, and initiation) 3a-g. The structures of all compounds were characterized by H-1 nuclear magnetic resonance (NMR) spectroscopy, C-13 NMR spectroscopy, infrared spectroscopy, and elemental analysis, which support the proposed structures. The structure of the 3c complex was determined by X-ray crystallography. More detailed structural characterization of the 3c complex was performed through single-crystal X-ray diffraction, which supports the proposed structures. The Pd-NHC-PEPPSI complexes were used as catalysts in the direct C-5-arylation of 2-acetyl furan, 2-acetylthiophene, and 2n-propylthiazole with different aryl bromides. These complexes exhibited moderate-to-high catalytic activities and selectively at the C-5 position. Furthermore, the Pd-NHC-PEPPSI complexes were evaluated for their potential antibacterial properties against a panel of bacterial strains, such as Micrococcus luteus, Listeria monocytogenes, Salmonella typhimurium, Staphylococcus aureus, Candida albicans, and Pseudomonas aeruginosa. The Pd-NHC-PEPPSI complex 3f showed better activity than ampicillin against Micrococcus luteus, with an MIC of 0.035 mg mL(-1). In addition, the antioxidant activities of the complexes 3d and 3f showed considerable free radical scavenging activity.en_US
dc.description.sponsorshipDeanship of Scientific Research [10091-alrasscac-bs-2020-1-3-I]en_US
dc.description.sponsorshipThe authors gratefully acknowledge Qassim University, represented by the Deanship of Scientific Research, on the financial support for this research under the number (10091-alrasscac-bs-2020-1-3-I) during the academic year 1442 AH/2020 AD.en_US
dc.identifier.doi10.1039/d1nj04606c
dc.identifier.endpage21262en_US
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue45en_US
dc.identifier.scopus2-s2.0-85120526865en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage21248en_US
dc.identifier.urihttps://doi.org/10.1039/d1nj04606c
dc.identifier.urihttps://hdl.handle.net/11616/100341
dc.identifier.volume45en_US
dc.identifier.wosWOS:000714122500001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherRoyal Soc Chemistryen_US
dc.relation.ispartofNew Journal of Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectDirect Arylationen_US
dc.subjectHeck Reactionsen_US
dc.subjectNhcen_US
dc.subjectReactivityen_US
dc.subjectTemperatureen_US
dc.subjectMechanismen_US
dc.subjectFuranen_US
dc.subjectSp(2)en_US
dc.subjectSp(3)en_US
dc.titleN-Heterocyclic carbene-palladium-PEPPSI complexes and their catalytic activity in the direct C-H bond activation of heteroarene derivatives with aryl bromides: synthesis, and antimicrobial and antioxidant activitiesen_US
dc.typeArticleen_US

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