Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi-Walled Carbon Nanotubes in Liquid Phase

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.

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carbon nanotubes, C−C coupling, heterogeneous catalysis, oxidative dehydrogenative coupling

DOI

10.1002/chem.201903054

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Wirtanen, T, Aikonen, S, Muuronen, M, Melchionna, M, Kemell, M, Davodi, F, Kallio, T, Hu, T & Helaja, J 2019, ' Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi-Walled Carbon Nanotubes in Liquid Phase ', Chemistry: A European Journal . https://doi.org/10.1002/chem.201903054

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https://urn.fi/URN:NBN:fi:aalto-202001021260

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[article-cris] Kemian tekniikan korkeakoulu / CHEM

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Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi-Walled Carbon Nanotubes in Liquid Phase

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