Browsing by Author "Wirtanen, Tom"

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  • Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi-Walled Carbon Nanotubes in Liquid Phase
    (2019-01-01) Wirtanen, Tom; Aikonen, Santeri; Muuronen, Mikko; Melchionna, Michele; Kemell, Marianna; Davodi, Fatemeh; Kallio, Tanja; Hu, Tao; Helaja, Juho
     A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
    HNO3-oxidized carbon nanotubes catalyze oxidative dehydrogenative (ODH) carbon–carbon bond formation between electron-rich (hetero)aryls with O2 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.