Ruthenium complexes of aminophosphine ligands and their use as pre-catalysts in the transfer hydrogenation of aromatic ketones: X-ray crystal structure of thiophene-2-(N-diphenylthiophosphino)methylamine

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dc.contributor.authorAydemir, Murat
dc.contributor.authorBaysal, Akin
dc.contributor.authorOzkar, Saim
dc.contributor.authorYildirim, Leyla Tatar
dc.date.accessioned2024-04-24T16:18:17Z
dc.date.available2024-04-24T16:18:17Z
dc.date.issued2011
dc.departmentDicle Üniversitesien_US
dc.description.abstractReaction of thiophene-2-methylamine with one or two equivalents of PPh2Cl in the presence of NEt3, proceeds in thf to give thiophene-2-(N-diphenylphosphino)methylamine, la and thiophene-2-(N, N-bis(diphenylphosphino))methylamine, 2a respectively, under anaerobic conditions. Oxidations of la and 2a with aqueous hydrogen peroxide, elemental sulfur or gray selenium in thf gives the corresponding oxides, sulfides and selenides [Ph2P(E)NHCH2-C4H3S] (E: O 1b, S 1c, Se 1d) and [(Ph2P(E))(2)NCH2-C4H3S], (E: O 2b, S 2c, Se 2d) respectively, in high yield. Furthermore, two novel Ru(II) complexes with the P-N ligands la and 2a were synthesized starting with the complex [Ru(eta(6)-p-cymene)(mu-Cl)Cl](2). The complexes were fully characterized by analytical and spectroscopic methods. P-31-{H-1} NMR, DEPT, H-1-13C HETCOR or H-1-H-1 COSY correlation experiments were used to confirm the spectral assignments. The molecular structure of thiophene-2-(N-diphenylthiophosphino)methylamine was also elucidated by single-crystal X-ray crystallography. Following activation by NaOH, compounds 3 and 4 catalyze the transfer hydrogenation of acetophenone derivatives to 1-phenylethanol derivatives in the presence of iso-PrOH as the hydrogen source. [Ru(Ph2PNHCH2-C4H3S)(eta(6)-p-cymene)Cl-2], 3 and [Ru((PPh2)(2)NCH2-C4H3S)-(eta(6)-p-cymene)Cl]Cl, 4 complexes are suitable catalyst precursors for the transfer hydrogenation of acetophenone derivatives in 0.1 M iso-PrOH solution. Notably 4 acts as an excellent catalyst giving the corresponding alcohols in excellent conversions up to 99% (TOF <= 744 h(-1)). This transfer hydrogenation is characterized by low reversibility under the experimental conditions. (C) 2010 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipTurkish Academy of Sciences; Dicle University [DUAPK 05-FF-27]en_US
dc.description.sponsorshipPartial support of this work by Turkish Academy of Sciences and Dicle University (Project number: DUAPK 05-FF-27) is gratefully acknowledged.en_US
dc.identifier.doi10.1016/j.poly.2010.12.011
dc.identifier.endpage804en_US
dc.identifier.issn0277-5387
dc.identifier.issue5en_US
dc.identifier.scopus2-s2.0-79952006894
dc.identifier.scopusqualityQ2
dc.identifier.startpage796en_US
dc.identifier.urihttps://doi.org/10.1016/j.poly.2010.12.011
dc.identifier.urihttps://hdl.handle.net/11468/15958
dc.identifier.volume30en_US
dc.identifier.wosWOS:000288922700016
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofPolyhedron
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectTransfer Hydrogenationen_US
dc.subjectCatalysisen_US
dc.subjectAminophosphineen_US
dc.subjectBis(Phosphino)Amineen_US
dc.subjectX-Ray Diffractionen_US
dc.titleRuthenium complexes of aminophosphine ligands and their use as pre-catalysts in the transfer hydrogenation of aromatic ketones: X-ray crystal structure of thiophene-2-(N-diphenylthiophosphino)methylamineen_US
dc.titleRuthenium complexes of aminophosphine ligands and their use as pre-catalysts in the transfer hydrogenation of aromatic ketones: X-ray crystal structure of thiophene-2-(N-diphenylthiophosphino)methylamine
dc.typeArticleen_US

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