Synthesis, structures, DFT calculations, and catalytic application in the direct arylation of five-membered heteroarenes with aryl bromides of novel palladium-N-heterocyclic carbene PEPPSI-type complexes

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dc.authoridBoulebd, Houssem/0000-0002-7727-8583
dc.authoridÖzdemir, Namık/0000-0003-3371-9874
dc.authoridGurbuz, Nevin/0000-0003-3201-3597
dc.authoridBoulebd, Houssem/0000-0002-7727-8583
dc.authoridOzdemir, Ismail/0000-0001-6325-0216
dc.authorwosidBoulebd, Houssem/HMP-2883-2023
dc.authorwosidÖzdemir, Namık/J-6434-2015
dc.authorwosidGurbuz, Nevin/A-3069-2016
dc.authorwosidBoulebd, Houssem/AAS-7080-2020
dc.contributor.authorSandeli, Abd el-Krim
dc.contributor.authorKhiri-Meribout, Naima
dc.contributor.authorBenzerka, Saida
dc.contributor.authorBoulebd, Houssem
dc.contributor.authorGurbuz, Nevin
dc.contributor.authorOzdemir, Namik
dc.contributor.authorOzdemir, Ismail
dc.date.accessioned2024-08-04T20:50:44Z
dc.date.available2024-08-04T20:50:44Z
dc.date.issued2021
dc.departmentİnönü Üniversitesien_US
dc.description.abstractA new series of Pd-catalysts based on an N-heterocyclic carbene PEPPSI-type ligand (PEPPSI = pyridine enhanced precatalyst preparation stabilization and initiation) with the general formula [Pd(H)Br2(NHC)(pyridine)] was synthesized and fully characterized via spectroscopic analytical methods. Further, the structural characterization of 3a, 3b, and 3d was performed via single-crystal X-ray diffraction, which supported the proposed structures and offered a more detailed structural characterization. Additionally, the electronic, vibrational, thermodynamic, and optical properties of 3a, as a representative molecule, were confirmed utilizing density functional theory (DFT) calculations. The experimental molecular geometry of the ground state of complex 3a was compared with the minimized structure obtained from DFT calculations. The B3LYP functional in conjunction with the LANL2DZ basis set for the palladium atom and the 6-311G(d,p) basis set for the hydrogen, carbon, nitrogen, and bromine atoms were used for all calculations. The frontier molecular orbitals and molecular electrostatic potential were also analyzed and discussed. Due to the significant interest in halo-substituted arylated heteroarenes in organic chemistry, the catalytic activity of these Pd(II)-NHC PEPPSI-type complexes were evaluated via the direct arylation of five-membered heteroaromatics such as thiophene, furan, and thiazole derivatives with various (hetero)aryl bromides in the presence of 1 mol% catalyst. The results showed that all new Pd-NHC complexes are effective catalysts, which exhibited very good catalytic activity and gave C-H activation selectively at the C(5)-position of 2-acetyl furan and 2-acetyl thiophene.en_US
dc.description.sponsorshipinonu University Research Fund [IU-BAP: FBG-2019-1594]; Scientific Research Projects Unit of Ondokuz Mays University [PYO.FEN.1906.19.001]en_US
dc.description.sponsorshipThe authors greatly acknowledge financial support from the inonu University Research Fund (IU-BAP: FBG-2019-1594) of this work. X-ray study was supported by the Scientific Research Projects Unit of Ondokuz Mays University (Project No: PYO.FEN.1906.19.001).en_US
dc.identifier.doi10.1039/d1nj03388c
dc.identifier.endpage17892en_US
dc.identifier.issn1144-0546
dc.identifier.issn1369-9261
dc.identifier.issue38en_US
dc.identifier.scopus2-s2.0-85116580903en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage17878en_US
dc.identifier.urihttps://doi.org/10.1039/d1nj03388c
dc.identifier.urihttps://hdl.handle.net/11616/100250
dc.identifier.volume45en_US
dc.identifier.wosWOS:000693600900001en_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.subjectCross-Coupling Reactionsen_US
dc.subjectMolecular Calculationsen_US
dc.subjectThiopheneen_US
dc.subjectLigandsen_US
dc.subjectChloropyrazinesen_US
dc.subjectBenzimidazoleen_US
dc.subjectHalidesen_US
dc.subjectFuranen_US
dc.titleSynthesis, structures, DFT calculations, and catalytic application in the direct arylation of five-membered heteroarenes with aryl bromides of novel palladium-N-heterocyclic carbene PEPPSI-type complexesen_US
dc.typeArticleen_US

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