The application of novel boron complexes in asymmetric transfer hydrogenation of aromatic ketones

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dc.contributor.authorTemel, Hamdi
dc.contributor.authorPasa, Salih
dc.contributor.authorAydemir, Murat
dc.date.accessioned2024-04-24T16:18:28Z
dc.date.available2024-04-24T16:18:28Z
dc.date.issued2015
dc.departmentDicle Üniversitesien_US
dc.description.abstractAsymmetric transfer hydrogenation using iso-PrOH as a hydrogen source offers an attractive route for reducing simple unsymmetrical functionalized ketones to chiral alcohols. The combined use of organometallic and coordination chemistry has produced a number of new and powerful synthetic methods for important classes of compounds in general and for optically active substances in particular. For this aim, the (S,Z)-1-((1-hydroxy butane-2-yl imino)methyl)naphthalene-2-ol chiral ligand was chosen to obtain boron complexes. Boronic derivative compounds such as phenylboronic acid, 6-methoxynaphthalen-2-ylboronic acid, 4-methyl-3-nitrophenylboronic acid and 1,4-phenylenediboronic acid were applied to obtain complexation with chiral based ligands. The structures of these ligands and their complexes have been elucidated by a combination of multinuclear NMR spectroscopy, LC MS/MS, TGA/DTA, UV Vis., elemental analysis, XRD, SEM, and FTIR. These boron complexes have also been tested as catalysts in the enantioselective transfer hydrogenation of acetophenone derivatives to afford the corresponding product, (S)-1-phenylethanol with high conversions (up to 99%) and modest enantioselectivities (up to 70% ee). The substituents on the backbone of the ligands had a significant effect on both the activity and % ee. (C) 2015 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipDicle University Research Fund (DUBAP) [14-FF-78, 14-EZF-14]; Scientific and Technological Research Council of Turkey (TUBITAK)en_US
dc.description.sponsorshipPartial support of this study by Dicle University Research Fund (DUBAP, Project numbers: 14-FF-78 and 14-EZF-14) and The Scientific and Technological Research Council of Turkey (TUBITAK) are gratefully acknowledged. We would like also thank to Dicle University Science and Technology Research Center (DUBTAM) for its kind contribution by offering analysis.en_US
dc.identifier.doi10.1016/j.tetasy.2015.08.007
dc.identifier.endpage1064en_US
dc.identifier.issn0957-4166
dc.identifier.issue18-19en_US
dc.identifier.scopus2-s2.0-84943232265
dc.identifier.scopusqualityN/A
dc.identifier.startpage1058en_US
dc.identifier.urihttps://doi.org/10.1016/j.tetasy.2015.08.007
dc.identifier.urihttps://hdl.handle.net/11468/16112
dc.identifier.volume26en_US
dc.identifier.wosWOS:000363077100005
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedron-Asymmetry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject[No Keyword]en_US
dc.titleThe application of novel boron complexes in asymmetric transfer hydrogenation of aromatic ketonesen_US
dc.titleThe application of novel boron complexes in asymmetric transfer hydrogenation of aromatic ketones
dc.typeArticleen_US

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