Palladium-Catalyzed Cross-Coupling Reaction via C-H Activation of Furanyl and Thiofuranyl Substrates

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dc.authoridOzdemir, Ismail/0000-0001-6325-0216
dc.authoridSEMERIL, David/0000-0002-2582-4191
dc.contributor.authorSahin, Neslihan
dc.contributor.authorOzdemir, Ismail
dc.contributor.authorSemeril, David
dc.date.accessioned2024-10-26T18:09:39Z
dc.date.available2024-10-26T18:09:39Z
dc.date.issued2024
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractThe present study explores the potential of four NHC-palladium(II) complexes derived from (Z)- or (E)-styryl-N-alkylbenzimidazolium salts, namely trans-dichloro-[(Z)-1-styryl- 3-benzyl-benzimidazol-2-yliden]pyridine palladium(II) (6), trans-dichloro-[(E)-1-styryl-3-benzyl- benzimidazol-2-yliden]pyridine palladium(II) (7), trans-dichloro-[(Z)-1-styryl-3-(3-fluorobenzyl)- benzimidazol-2-yliden]pyridine palladium(II) (8) and trans-dichloro-[(E)-1-styryl-3- (3-fluorobenzyl)-benzimidazol-2-yliden]pyridine palladium(II) (9), to be use as pre-catalysts for the cross-coupling reactions between furanyl or thiofuranyl derivatives and arylbromides via the C-H activation of the heterocycles. The structures of the four Pd(II) complexes have been elucidated through the use of multinuclear NMR, FT-IR and mass spectroscopy. Furthermore, the cis or trans conformation of the styryl substituents and the geometry of two different compounds was substantiated by single-crystal X-ray diffraction, which was carried out on organometallic species 6, 8 and 9. After the optimization of catalytic conditions, which was carried out with 1 mol% of pre-catalyst with KOAc as a base in dimethylacetamide at 120 degrees C for 3 h, complex 6 proved to be the most effective pre-catalyst agent, with full or quasi full conversions being observed in the cross-coupling of 4-bromoacetophenone with 2-butylfuran, 1-(2-furanyl)-ethanone, furfuryl acetate, furfural, 1-(2-thienyl)-ethanone, thenaldehyde and 2-methylthiophene.
dc.description.sponsorshipScientific and Technological Research of Turkey [TUBITAK-2219]
dc.description.sponsorshipN.& Scedil;. thanks the Scientific and Technological Research of Turkey (TUBITAK-2219-International Postdoctoral Research Scholarship Program) for a research fellowship.
dc.identifier.doi10.3390/inorganics12060175
dc.identifier.issn2304-6740
dc.identifier.issue6
dc.identifier.scopus2-s2.0-85196901098
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.3390/inorganics12060175
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30206
dc.identifier.volume12
dc.identifier.wosWOS:001256696000001
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherMdpi
dc.relation.ispartofInorganics
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectpalladium
dc.subjectbenzimidazolium salt
dc.subjectstyryl substituent
dc.subjecthomogeneous catalysis
dc.subjectcross-coupling
dc.subjectC-H activation
dc.titlePalladium-Catalyzed Cross-Coupling Reaction via C-H Activation of Furanyl and Thiofuranyl Substrates
dc.typeArticle

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