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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.descriptionWOS: 000318240600013en_US
dc.description.abstractThree imidazolium salts based on a rigid resorcinarene platform (13) were synthesised and used as catalyst precursors in the SuzukiMiyaura cross-coupling of aryl halides with phenylboronic acid. In these pro-carbene ligands, the heterocyclic moiety has one N atom connected to a C2 atom of a resorcinolic ring, and the other is substituted by an alkyl group (R=n-propyl, iso-propyl, benzyl). The methinic C atoms of the macrocyclic core are all substituted by a pentyl group. The best catalytic performances were obtained by using an imidazolium/Pd ratio of 1:1. The catalytic systems displayed high activities, which increased in the order R=n-propyl(1)<i-propyl(2)<benzyl(3). For example, the use of 3 resulted in activities up to 30100mol(converted ArX)mol(Pd)1h1 in the arylation of bromotoluene at 100 degrees C in dioxane. Comparative studies showed that the performance of imidazolium salt 3 is significantly superior to that of related salts devoid of a cavity-shaped substituent. These experiments illustrate the role of the bulky resorcinarene unit, which facilitates the reductive elimination step. Modification of the cavitand structure by replacement of the pentyl substituents with phenyl groups further revealed that the catalytic outcome is influenced by the nature of the lower belt-substituents. The results strongly suggest that the Pd catalysts obtained from 13 have the metal centre preferentially located outside the cavity.en_US
dc.description.sponsorshipscientific and technological research of Turkey (TUBITAK-BIDEB); International Research Fellowship Programmeen_US
dc.description.sponsorshipThe authors thank the scientific and technological research of Turkey (TUBITAK-BIDEB) and the International Research Fellowship Programme for the grant to N.S. Grateful acknowledgement is due to Johnson Matthey for a loan of palladium.en_US
dc.publisherWILEY-V C H VERLAG GMBHen_US
dc.subjectnitrogen heterocyclesen_US
dc.titleResorcinarene-Functionalised Imidazolium Salts as Ligand Precursors for Palladium-Catalysed SuzukiMiyaura Cross-Couplingsen_US
dc.contributor.department[Sahin, Neslihan -- Semeril, David -- Brenner, Eric -- Matt, Dominique] Univ Strasbourg, CNRS, Lab Chim Inorgan Mol & Catalyse, UMR 7177, F-67008 Strasbourg, France -- [Ozdemir, Ismail] Inonu Univ, Dept Chem, Fac Sci & Art, TR-44280 Malatya, Turkey -- [Sahin, Neslihan -- Kaya, Cemal] Cumhuriyet Univ, Fac Sci, Dept Chem, TR-58140 Sivas, Turkey -- [Toupet, Loic] Univ Rennes 1, Inst Phys, CNRS, UMR 6251, F-35042 Rennes, Franceen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US

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