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Insights into reactivity patterns of Ag(II)SO4 with respect to fluoro- and trifluoromethyl-substituted aromatics

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dc.abstract.enDirect oxidative functionalization of C–H bonds is an ongoing chemical challenge. Here we report results of the comparative tests of Ag(II)SO4 reactivity towards 24 selected fluoro- and/or trifluoromethyl-substituted aromatic hydrocarbons with ionization potentials (IP) varying in the 8.15–10.72 eV range. For many of those we observed the oxidative C–C coupling reactions and/or O-insertion in the C–H bonds. Observed differences in reactivity of organic substrates are explained on the basis of their IP values on one side, free Gibbs energy of the heterolytic C–H bond cleavage on the other, as well as impact of the steric hindrance effect of CF3- groups. The electron affinity of the surface of solid Ag(II)SO4 was estimated at ca. 9.3 eV. Interesting Brønsted acid-induced side reaction of the protolytic C–F bond activation, followed by conversion of the trifluoromethyl group to esters of hexafluoro-i-propanol or nonafluoro-t-butanol used as reaction medium, has been observed for 1-(trifluoromethyl)naphthalene.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorGrzeszkiewicz, Mikołaj
dc.contributor.authorMalinowski, Przemysław
dc.contributor.authorBudniak, Adam K.
dc.contributor.authorLeszczyński, Piotr
dc.contributor.authorCyrański, Michał
dc.contributor.authorMazej, Zoran
dc.contributor.authorJaroń, Tomasz
dc.contributor.authorDobrzycki, Łukasz
dc.contributor.authorSzarek, Paweł
dc.contributor.authorGawraczyński, Jakub
dc.contributor.authorGrochala, Wojciech
dc.date.accessioned2024-01-25T04:19:44Z
dc.date.available2024-01-25T04:19:44Z
dc.date.issued2019
dc.description.financeNie dotyczy
dc.description.volume218
dc.identifier.doi10.1016/J.JFLUCHEM.2018.12.002
dc.identifier.issn0022-1139
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/109365
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofJournal of Fluorine Chemistry
dc.relation.pages105-110
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.subject.enFluoroaromatics
dc.subject.enO atom insertion
dc.subject.enOxidative C–C coupling
dc.subject.enSilver(2+)
dc.subject.enTrifluoromethylaromatics
dc.titleInsights into reactivity patterns of Ag(II)SO4 with respect to fluoro- and trifluoromethyl-substituted aromatics
dc.typeJournalArticle
dspace.entity.typePublication