Cross-coupling reactions in water using ionic liquid-based palladium(II)-phosphinite complexes as outstanding catalysts

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dc.contributor.authorMeriç, Nermin
dc.contributor.authorAydemir, Murat
dc.contributor.authorIşık, Uğur
dc.contributor.authorOcak, Yusuf Selim
dc.contributor.authorRafikova, Khadichakhan
dc.contributor.authorPaşa, Salih
dc.contributor.authorKayan, Cezmi
dc.contributor.authorDurap, Feyyaz
dc.contributor.authorTemel, Hamdi
dc.contributor.authorZazybin, Alexey G.
dc.contributor.orcid0000-0003-0899-1948
dc.contributor.orcid0000-0002-6244-9327
dc.contributor.orcid0000-0002-4792-8821
dc.date.accessioned2024-04-24T15:59:19Z
dc.date.available2024-04-24T15:59:19Z
dc.date.issued2014
dc.departmentDicle Üniversitesi, Fen Fakültesi, Kimya Bölümüen_US
dc.description.abstractTwo new phosphinite ligands based on ionic liquids [(Ph2PO)C7H14N2Cl]Cl (1) and [(Cy2PO)C7H14N2Cl]Cl (2) were synthesized by reaction of 1-(3-chloro-2-hydoxypropyl)-3-methylimidazolium chloride, [C7H15N2OCl]Cl, with one equivalent of chlorodiphenylphosphine or chlorodicyclohexylphosphine, respectively, in anhydrous CH2Cl2 and under argon atmosphere. The reactions of 1 and 2 with MCl2(cod) (M=Pd, Pt; cod=1,5-cyclooctadiene) yield complexes cis-[M([(Ph2PO)C7H14N2Cl]Cl)(2)Cl-2] and cis-[M(Cy2PO)C7H14N2Cl]Cl)(2)Cl-2], respectively. All complexes were isolated as analytically pure substances and characterized using multi-nuclear NMR and infrared spectroscopies and elemental analysis. The catalytic activity of palladium complexes based on ionic liquid phosphinite ligands 1 and 2 was investigated in Suzuki cross-coupling. They show outstanding catalytic activity in coupling of a series of aryl bromides or aryl iodides with phenylboronic acid under the optimized reaction conditions in water. The complexes provide turnover frequencies of 57 600 and 232 800h(-1) in Suzuki coupling reactions of phenylboronic acid with p-bromoacetophenone or p-iodoacetophenone, respectively, which are the highest values ever reported among similar complexes for Suzuki coupling reactions in water as sole solvent in homogeneous catalysis. Furthermore, the palladium complexes were also found to be highly active catalysts in the Heck reaction affording trans-stilbenes. Copyright (c) 2014 John Wiley & Sons, Ltd.en_US
dc.description.sponsorshipDicle University [DUBAP-07-01-22, 12-FF-140]en_US
dc.description.sponsorshipPartial support from Dicle University (project number: DUBAP-07-01-22 and 12-FF-140) is gratefully acknowledged.en_US
dc.identifier.citationMeriç, N., Aydemir, M., Işık, U., Ocak, Y. S., Rafikova, K., Paşa, S. ve diğerleri. (2014). Cross-coupling reactions in water using ionic liquid-based palladium(II)-phosphinite complexes as outstanding catalysts. Journal of Pharmacy and Pharmacology, 28(11), 818-825.
dc.identifier.doi10.1002/aoc.3205
dc.identifier.endpage825en_US
dc.identifier.issn0268-2605
dc.identifier.issn1099-0739
dc.identifier.issue11en_US
dc.identifier.scopus2-s2.0-84915753336
dc.identifier.scopusqualityQ1
dc.identifier.startpage818en_US
dc.identifier.urihttps://doi.org/10.1002/aoc.3205
dc.identifier.urihttps://hdl.handle.net/11468/13966
dc.identifier.urihttps://onlinelibrary.wiley.com/doi/epdf/10.1002/aoc.3205
dc.identifier.volume28en_US
dc.identifier.wosWOS:000344005400004
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.ispartofApplied Organometallic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectIonic Liquiden_US
dc.subjectPhosphiniteen_US
dc.subjectSuzuki couplingen_US
dc.subjectHeck reactionen_US
dc.subjectPalladiumen_US
dc.subjectPlatinumen_US
dc.titleCross-coupling reactions in water using ionic liquid-based palladium(II)-phosphinite complexes as outstanding catalystsen_US
dc.titleCross-coupling reactions in water using ionic liquid-based palladium(II)-phosphinite complexes as outstanding catalysts
dc.typeArticleen_US

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