Please use this identifier to cite or link to this item: https://hdl.handle.net/11147/4981
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dc.contributor.authorÜçüncü, Muhammed-
dc.contributor.authorKarakuş, Erman-
dc.contributor.authorKuş, Melih-
dc.contributor.authorAkpınar, Gürkan Eray-
dc.contributor.authorAksın Artok, Özge-
dc.contributor.authorKrause, Norbert-
dc.contributor.authorKaraca, Sıla-
dc.contributor.authorElmaci, Nuran-
dc.contributor.authorArtok, Levent-
dc.date.accessioned2017-03-06T12:04:27Z-
dc.date.available2017-03-06T12:04:27Z-
dc.date.issued2011-08-
dc.identifier.citationÜçüncü, M., Karakuş, E., Kuş, M., Akpınar, G.E., Aksın Artok, Ö., Krause, N., Karaca, S., Elmacı, N., and Artok, L. (201). Rhodium- and palladium-catalyzed 1,5-substitution reactions of 2-En-4-yne acetates and carbonates with organoboronic acids. American Chemical Society, 76(15), 5959-5971. doi:10.1021/jo200201ren_US
dc.identifier.issn0022-3263-
dc.identifier.issn0022-3263-
dc.identifier.urihttp://doi.org/10.1021/jo200201r-
dc.identifier.urihttp://hdl.handle.net/11147/4981-
dc.description.abstractTwo methods involving the rhodium-catalyzed reaction of 2-en-4-yne acetates and the palladium-catalyzed reaction of 2-en-4-yne carbonates with organoboronic acids were investigated; both afforded exclusively the (E)-configured vinylallenes. The coordinative interaction of the rhodium with the acetate group promoted the δ-elimination of Rh(I)-OAc from the alkenylrhodium intermediate II in both syn and anti modes, with the syn-elimination being the major path. DFT calculations revealed that a conformer of this intermediate (II), which can lead to the (E)-configured vinylallene product via the syn-elimination mode, is energetically the most favorable conformer. The rhodium-catalyzed procedure is not applicable to reactions involving (E)-configured enyne acetates, because the geometry of the alkenylrhodium intermediate that is derived from the corresponding (E)-enyne acetate would not allow such coordinative interaction to occur. The palladium-catalyzed method, which proceeds through formation of the σ-vinylallenylpalladium intermediate, B, is suitable for both the (E)- and (Z)-configured enyne carbonates and appears to have a wider scope for both organoboronic acids and enyne substrates. The palladium-catalyzed reaction of an enantiomerically enriched enyne carbonate proceeded with racemization.en_US
dc.description.sponsorshipThe Scientific and Technological Research Council of Turkey and Federal Ministry of Education and Research (Germany) via the Intensified Cooperation Program (210T092)en_US
dc.language.isoenen_US
dc.publisherAmerican Chemical Societyen_US
dc.relation.ispartofJournal of Organic Chemistryen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectAcetate groupsen_US
dc.subjectDFT calculationen_US
dc.subjectOrganoboronic acidsen_US
dc.subjectPalladium-catalyzed reactionsen_US
dc.subjectRhodium-catalyzeden_US
dc.subjectOrganometallicsen_US
dc.titleRhodium- and palladium-catalyzed 1,5-substitution reactions of 2-En-4-yne acetates and carbonates with organoboronic acidsen_US
dc.typeArticleen_US
dc.authoridTR114736en_US
dc.authoridTR113970en_US
dc.authoridTR9101en_US
dc.authoridTR1860en_US
dc.institutionauthorÜçüncü, Muhammed-
dc.institutionauthorKarakuş, Erman-
dc.institutionauthorKuş, Melih-
dc.institutionauthorAkpınar, Gürkan Eray-
dc.institutionauthorKaraca, Sıla-
dc.institutionauthorNuran, Elmacı-
dc.institutionauthorArtok, Levent-
dc.departmentİzmir Institute of Technology. Chemistryen_US
dc.identifier.volume76en_US
dc.identifier.issue15en_US
dc.identifier.startpage5959en_US
dc.identifier.endpage5971en_US
dc.identifier.wosWOS:000293252600009en_US
dc.identifier.scopus2-s2.0-79961038042en_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.identifier.doi10.1021/jo200201r-
dc.identifier.pmid21662974en_US
dc.relation.doi10.1021/jo200201ren_US
dc.coverage.doi10.1021/jo200201ren_US
dc.identifier.wosqualityQ1-
dc.identifier.scopusqualityN/A-
item.grantfulltextopen-
item.openairetypeArticle-
item.fulltextWith Fulltext-
item.cerifentitytypePublications-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.languageiso639-1en-
crisitem.author.dept04.01. Department of Chemistry-
crisitem.author.dept04.01. Department of Chemistry-
crisitem.author.dept04.01. Department of Chemistry-
Appears in Collections:Chemistry / Kimya
PubMed İndeksli Yayınlar Koleksiyonu / PubMed Indexed Publications Collection
Scopus İndeksli Yayınlar Koleksiyonu / Scopus Indexed Publications Collection
WoS İndeksli Yayınlar Koleksiyonu / WoS Indexed Publications Collection
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