Subtle Steric Effects in Nickel-Catalysed Kumada-Tamao-Corriu Cross-Coupling Using Resorcinarenyl-Imidazolium Salts

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dc.authoridÖzdemir, İsmail/0000-0001-6325-0216
dc.authorwosidTOUPET, Loic/N-7043-2014
dc.authorwosidŞAHİN, Neslihan/F-6402-2019
dc.authorwosidÖzdemir, İsmail/ABI-5192-2020
dc.contributor.authorSahin, Neslihan
dc.contributor.authorSemeril, David
dc.contributor.authorBrenner, Eric
dc.contributor.authorMatt, Dominique
dc.contributor.authorOzdemir, Ismail
dc.contributor.authorKaya, Cemal
dc.contributor.authorToupet, Loic
dc.date.accessioned2024-08-04T20:37:42Z
dc.date.available2024-08-04T20:37:42Z
dc.date.issued2013
dc.departmentİnönü Üniversitesien_US
dc.description.abstractThree resorcinarene-cavitands bearing a 3-R-1-imidazolylium substituent (R = alkyl) grafted to the wider rim of the cavitand (1-3) were assessed in the Kumada-Tamao-Corriu cross-coupling of aryl halides with arylmagnesium halides. Their combination with [Ni(cod)(2)] (cod = 1,5-cyclooctadiene; 1:1 stoichiometry) resulted in highly efficient catalysts, the activities of which varied in the following order: R = n-propyl (1) < isopropyl (2) approximate to benzyl (3). A remarkable turnover frequency of 60400 mol(ArX) mol(Ni)(-1) h(-1) was obtained in the coupling of 2-bromo-6-methoxynaphthalene with PhMgBr (100 degrees C in dioxane, with precursor 2). The high activities of the cavitand derivatives were attributed to steric effects that facilitate the reductive-elimination/product decoordination step. Comparative experiments carried out with a structurally modified resorcinarene, as well as cavity-free imidazolium salts bearing 2-methoxyaryl substituents, suggest that the efficiency of the catalysts mainly relies on steric interactions between the metal and the flexible substituents attached to two methine carbon atoms. These steric interactions are probably reinforced each time the metal binds one of the two oxygen atoms located next to the catalytic centre.en_US
dc.description.sponsorshipScientific and Technological Research of Turkey (TUBITAK-BIDEB); French Agence Nationale de la Recherche (ANR) [ANR-12-BS07-0001-01-RESICAT]en_US
dc.description.sponsorshipThe authors thank the Scientific and Technological Research of Turkey (TUBITAK-BIDEB), International Research Fellowship Programme for a grant to N. S., and the French Agence Nationale de la Recherche (ANR) (ANR-12-BS07-0001-01-RESICAT) for financial support.en_US
dc.identifier.doi10.1002/ejoc.201300347
dc.identifier.endpage4449en_US
dc.identifier.issn1434-193X
dc.identifier.issn1099-0690
dc.identifier.issue20en_US
dc.identifier.scopus2-s2.0-84879886188en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage4443en_US
dc.identifier.urihttps://doi.org/10.1002/ejoc.201300347
dc.identifier.urihttps://hdl.handle.net/11616/96125
dc.identifier.volume2013en_US
dc.identifier.wosWOS:000321737700033en_US
dc.identifier.wosqualityQ1en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherWiley-V C H Verlag Gmbhen_US
dc.relation.ispartofEuropean Journal of Organic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectCavitandsen_US
dc.subjectCross-coupling reactionsen_US
dc.subjectLigand designen_US
dc.subjectCarbene ligandsen_US
dc.subjectNickelen_US
dc.titleSubtle Steric Effects in Nickel-Catalysed Kumada-Tamao-Corriu Cross-Coupling Using Resorcinarenyl-Imidazolium Saltsen_US
dc.typeArticleen_US

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