Reconnaissance of reactivity of an Ag(ii )SO4 one-electron oxidizer towards naphthalene derivatives
| Autor: | Piotr J. Leszczyński, Jakub Gawraczyński, Zoran Mazej, Wojciech Grochala, Łukasz Dobrzycki, Karol J. Fijalkowski, Mikołaj Grzeszkiewicz, Kristina Prezelj, Adam Budniak, Michał K. Cyrański, Wiktor Koźmiński, Michał Masny |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry General Chemistry Electron 010402 general chemistry Photochemistry 01 natural sciences Catalysis 0104 chemical sciences Divalent Coupling (electronics) chemistry.chemical_compound chemistry Reagent Polymer chemistry Halogen Materials Chemistry Oxidative coupling of methane Reactivity (chemistry) Naphthalene |
| Zdroj: | New Journal of Chemistry. 41:10742-10749 |
| ISSN: | 1369-9261 1144-0546 |
| DOI: | 10.1039/c7nj02299a |
| Popis: | We 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. |
| Databáze: | OpenAIRE |
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