Direct arylation of heteroarenes by PEPPSI-type palladium-NHC complexes and representative quantum chemical calculations for the compound which the structure was determined by X-ray crystallography

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dc.authoridOzdemir, Ismail/0000-0001-6325-0216
dc.authoridTahir, Dr. Muhammad Nawaz/0000-0002-6815-9806
dc.contributor.authorSahin, Neslihan
dc.contributor.authorSerdaroglu, Goncagul
dc.contributor.authorDusunceli, Serpil Demir
dc.contributor.authorTahir, Muhammad Navaz
dc.contributor.authorArici, Cengiz
dc.contributor.authorOzdemir, Ismail
dc.date.accessioned2024-10-26T18:09:52Z
dc.date.available2024-10-26T18:09:52Z
dc.date.issued2019
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractIn this study, we synthesized five new PEPPSI-type Pd-NHC complexes with high yields around 78-83%. The structures of all complexes were characterized by FT-IR, H-1 NMR, and C-13{H-1} NMR spectroscopies. Further, the structure of 2c was determined by X-ray crystallography. The single-crystal structure of 2c shows that coordination geometry around Pd is distorted square planar. The Pd-NHC complexes were efficient catalysts for the direct C5-arylation of 2-n-butylthiazole, 2-n-butylfuran, and 2-n-butylthiophene with various aryl-bromides and showed high catalytic activity for arylation reaction using only 1 mol% catalyst loading at 130 degrees C for 1 h. The conversions for substrates containing electron-withdrawing groups were higher than for substituents containing electron-donating groups. In order to evaluate the catalytic activity of the complexes, representative electronic and spectroscopic simulations by DFT method have been performed for 2c. NBO analysis has revealed that the strongest interaction contributing to the lowering of the molecular stabilization energy for 2c is predicted as pi(C11-N27) -> pi*(N26-C28) with E-(2) = 73.93 kcal mol(-1). In addition, FMO analysis has implied that 2c is more chemically reactive because of its lower energy gap value. According to the other quantum chemical parameters, 2c is softer, better electrophile and has more charge-transfer capability than 1c.
dc.description.sponsorshipSivas Cumhuriyet University, Scientific Research Projects Department [CUBAP: EGT-066]
dc.description.sponsorshipThis work was supported by Sivas Cumhuriyet University, Scientific Research Projects Department (Project No: CUBAP: EGT-066). All calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e-Infrastructure).
dc.identifier.doi10.1080/00958972.2019.1692202
dc.identifier.endpage3284
dc.identifier.issn0095-8972
dc.identifier.issn1029-0389
dc.identifier.issue19-21
dc.identifier.scopus2-s2.0-85075389114
dc.identifier.scopusqualityQ3
dc.identifier.startpage3258
dc.identifier.urihttps://doi.org/10.1080/00958972.2019.1692202
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30320
dc.identifier.volume72
dc.identifier.wosWOS:000498087900001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherTaylor & Francis Ltd
dc.relation.ispartofJournal of Coordination Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectPEPPSI
dc.subjectN-heterocyclic carbine
dc.subjectX-ray structure
dc.subjectdirect arylation
dc.subjectquantum chemical calculations
dc.titleDirect arylation of heteroarenes by PEPPSI-type palladium-NHC complexes and representative quantum chemical calculations for the compound which the structure was determined by X-ray crystallography
dc.typeArticle

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