Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi‐Walled Carbon Nanotubes in Liquid Phase
| Autor: | Tanja Kallio, Fatemeh Davodi, Tom Wirtanen, Michele Melchionna, Mikko Muuronen, Juho Helaja, Marianna Kemell, Tao Hu, Santeri Alfred Arttu Aikonen |
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| Přispěvatelé: | Wirtanen, T., Aikonen, S., Muuronen, M., Melchionna, M., Kemell, M., Davodi, F., Kallio, T., Hu, T., Helaja, J., Department, Department of Chemistry, Juho Pekka Helaja / Principal Investigator, University of Helsinki, Università Degli Studi di Trieste, Department of Chemistry and Materials Science, University of Oulu, Aalto-yliopisto, Aalto University |
| Rok vydání: | 2019 |
| Předmět: |
Reaction mechanism
116 Chemical sciences oxidative dehydrogenative coupling Liquid phase Oxidative phosphorylation Carbon nanotube 010402 general chemistry Heterogeneous catalysis 01 natural sciences Catalysis law.invention law carbon nanotube carbon nanotubes biology 010405 organic chemistry Chemistry Organic Chemistry C−C coupling Cationic polymerization heterogeneous catalysis Active site General Chemistry Combinatorial chemistry 0104 chemical sciences biology.protein heterogeneous catalysi Titration C-C coupling |
| Zdroj: | Chemistry – A European Journal. 25:12288-12293 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.201903054 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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