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Reconnaissance of reactivity of an Ag(II)SO4 one-electron oxidizer towards naphthalene derivatives

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dc.abstract.enWe test divalent silver sulphate, Ag(II)SO4 as a novel reagent for oxidative coupling of aromatic hydrocarbons under ambient temperature conditions. The applicability of the C(sp2)–C(sp2) coupling protocol is illustrated for naphthalene and its 1-substituted derivatives containing either electron donating (e.g. Me, MeO, or Ph) or electron-withdrawing groups (X = F⋯I), leading to 4,4′-disubstituted-1,1′-binaphthyls. Coupling of 2-bromo-naphthalene yields a mixture of 2,2′-, 2,7′-, and 7,7′-dibromo-1,1′-binaphthyls together with their trimeric and tetrameric analogues. The coupling of strongly electron-withdrawing 1-CF3-naphthalene provides the 5,5′-disubstituted-1,1′-binaphthyl derivative. The new method does not require the presence of halogen substituents, in contrast to most of the known C–C coupling methods, and it preserves them, if present. Ag(II)SO4 may be easily electrochemically regenerated from the Ag(I)HSO4 byproduct. However, the C–C coupling method currently suffers from low yields, up to 17%, and it requires further optimization
dc.affiliationUniwersytet Warszawski
dc.contributor.authorFijałkowski, Karol
dc.contributor.authorLeszczyński, Piotr
dc.contributor.authorBudniak, Adam Krzysztof
dc.contributor.authorCyrański, Michał
dc.contributor.authorGrzeszkiewicz, Mikołaj
dc.contributor.authorMazej, Zoran
dc.contributor.authorMasny, Michał
dc.contributor.authorPrezelj, Kristina
dc.contributor.authorDobrzycki, Łukasz
dc.contributor.authorKoźmiński, Wiktor
dc.contributor.authorGawraczyński, Jakub
dc.contributor.authorGrochala, Wojciech
dc.date.accessioned2024-01-25T18:57:58Z
dc.date.available2024-01-25T18:57:58Z
dc.date.issued2017
dc.description.financeNie dotyczy
dc.description.number19
dc.description.volume41
dc.identifier.doi10.1039/C7NJ02299A
dc.identifier.issn1144-0546
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/118038
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofNew Journal of Chemistry
dc.relation.pages10742-10749
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleReconnaissance of reactivity of an Ag(II)SO4 one-electron oxidizer towards naphthalene derivatives
dc.typeJournalArticle
dspace.entity.typePublication