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RESEARCH PRODUCT
Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi‐Walled Carbon Nanotubes in Liquid Phase
Tanja KallioFatemeh DavodiTom WirtanenTom WirtanenMichele MelchionnaMikko MuuronenJuho HelajaMarianna KemellTao HuSanteri Alfred Arttu Aikonensubject
Reaction mechanism116 Chemical sciencesoxidative dehydrogenative couplingLiquid phaseOxidative phosphorylationCarbon nanotube010402 general chemistryHeterogeneous catalysis01 natural sciencesCatalysislaw.inventionlawcarbon nanotubecarbon nanotubesbiology010405 organic chemistryChemistryOrganic ChemistryC−C couplingCationic polymerizationcarbon nanotubes; C−C coupling; heterogeneous catalysis; oxidative dehydrogenative couplingActive siteGeneral ChemistryCombinatorial chemistry0104 chemical sciencesheterogeneous catalysisbiology.proteinheterogeneous catalysiTitrationC-C couplingdescription
HNO3-oxidized carbon nanotubes catalyze oxidative dehydrogenative (ODH) carbon-carbon bond formation between electron-rich (hetero)aryls with O-2 as a terminal oxidant. The recyclable carbocatalytic method provides a convenient and an operationally easy synthetic protocol for accessing various benzofused homodimers, biaryls, triphenylenes, and related benzofused heteroaryls that are highly useful frameworks for material chemistry applications. Carbonyls/quinones are the catalytically active site of the carbocatalyst as indicated by model compounds and titration experiments. Further investigations of the reaction mechanism with a combination of experimental and DFT methods support the competing nature of acid-catalyzed and radical cationic ODHs, and indicate that both mechanisms operate with the current material. Peer reviewed
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-01-01 | Chemistry – A European Journal |