Plausible PEPPSI catalysts for direct C-H functionalization of five-membered heterocyclic bioactive motifs: synthesis, spectral, X-ray crystallographic characterizations and catalytic activity

Basit Öğe Kaydı
dc.authoridGurbuz, Nevin/0000-0003-3201-3597
dc.authorwosidOZDEMIR, ISMAIL/KVY-3420-2024
dc.authorwosidMansour, Lamjed/AAD-8613-2019
dc.authorwosidGurbuz, Nevin/A-3069-2016
dc.contributor.authorBensalah, Donia
dc.contributor.authorMansour, Lamjed
dc.contributor.authorSauthier, Mathieu
dc.contributor.authorGurbuz, Nevin
dc.contributor.authorOzdemir, Ismail
dc.contributor.authorBeji, Lotfi
dc.contributor.authorGatri, Rafik
dc.date.accessioned2024-08-04T20:54:50Z
dc.date.available2024-08-04T20:54:50Z
dc.date.issued2023
dc.departmentİnönü Üniversitesien_US
dc.description.abstractIn this study, a series of benzimidazolium salts were synthesized as asymmetric N-heterocyclic carbene (NHC) precursors. Nine novel palladium complexes with the general formula [PdX2(NHC)(pyridine)] were synthesized using benzimidazolium salts in the PEPPSI (Pyridine Enhanced Precatalyst Preparation, Stabilization and Initiation) theme. All synthesized Pd(ii) complexes are stable. The synthesized compounds were thoroughly characterized by respective spectroscopic techniques, such as 1HNMR, 13C NMR, FTIR spectroscopy, X-ray crystallography and elemental analysis. The geometric structure of the palladium N-heterocyclic carbene has been optimized in the framework of density functional theory (DFT) using the B3LYP-D3 dispersion functional with LANL2DZ as a basis set. The on/off mechanism of pyridine assisted Pd-NHC complexes made them the best C-H functionalized catalysts for regioselective C-5 arylated products. Five membered heterocyclic compounds such as 2-acetyl furan, furfuryl acetate 2-acetylthiophene and N-methylpyrrole-2-carboxaldehyde were treated with numerous aryl bromides and arylchlorides under optimal catalytic reaction conditions. Interestingly, all the prepared catalysts possessed essential structural features that facilitated the formation of desired coupling products in quantitative yield with excellent selectivity. The arylation reaction of bromoacetophenone was highly catalytically active with only 1 mol% catalyst loading at 150 degrees C for 2 hours. To check the efficiency of the synthesized complexes, three different five member heterocyclic substrates (2-acetylfuran, 2-acetylthiophen, 2-propylthaizole) were tested with a number of aryl bromides bearing both electron-donating and electron-withdrawing groups on para position. The data in Tables 2-4. Indicated that electron-donating groups on the para position of aryl halide decreased the catalytic conversion while electron-withdrawing groups increased the catalytic conversion this was due to the high nucleophilicity of the electron-donating substituents. In this study, a series of benzimidazolium salts were synthesized as asymmetric N-heterocyclic carbene (NHC) precursors.en_US
dc.description.sponsorshipThe authors extended their appreciation to the Researchers Supporting Project number (RSP2023R75), King Saud University, Riyadh, Saudi Arabia. [RSP2023R75]; King Saud University, Riyadh, Saudi Arabiaen_US
dc.description.sponsorshipThe authors extended their appreciation to the Researchers Supporting Project number (RSP2023R75), King Saud University, Riyadh, Saudi Arabia.en_US
dc.identifier.doi10.1039/d3ra06334h
dc.identifier.endpage31410en_US
dc.identifier.issn2046-2069
dc.identifier.issue45en_US
dc.identifier.pmid37941793en_US
dc.identifier.scopus2-s2.0-85177049022en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage31386en_US
dc.identifier.urihttps://doi.org/10.1039/d3ra06334h
dc.identifier.urihttps://hdl.handle.net/11616/101677
dc.identifier.volume13en_US
dc.identifier.wosWOS:001095875600001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherRoyal Soc Chemistryen_US
dc.relation.ispartofRsc Advancesen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectCross-Coupling Reactionen_US
dc.subjectDirect Arylationen_US
dc.subjectCarbene Complexesen_US
dc.subjectPalladium Complexesen_US
dc.subjectDesulfitative Arylationen_US
dc.subjectHeterogeneous Catalysisen_US
dc.subjectCoordination-Compoundsen_US
dc.subjectBond Activationen_US
dc.subjectAryl Bromidesen_US
dc.subjectMechanismen_US
dc.titlePlausible PEPPSI catalysts for direct C-H functionalization of five-membered heterocyclic bioactive motifs: synthesis, spectral, X-ray crystallographic characterizations and catalytic activityen_US
dc.typeArticleen_US

Dosyalar

Koleksiyon

WoS İndeksli Yayınlar Koleksiyonu
PubMed İndeksli Yayın Koleksiyonu
Scopus İndeksli Yayınlar Koleksiyonu