TY - JOUR
T1 - Carbocatalytic Oxidative Dehydrogenative Couplings of (Hetero)Aryls by Oxidized Multi-Walled Carbon Nanotubes in Liquid Phase
AU - Wirtanen, Tom
AU - Aikonen, Santeri
AU - Muuronen, Mikko
AU - Melchionna, Michele
AU - Kemell, Marianna
AU - Davodi, Fatemeh
AU - Kallio, Tanja
AU - Hu, Tao
AU - Helaja, Juho
PY - 2019/1/1
Y1 - 2019/1/1
N2 - 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.
AB - 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.
KW - carbon nanotubes
KW - C−C coupling
KW - heterogeneous catalysis
KW - oxidative dehydrogenative coupling
UR - http://www.scopus.com/inward/record.url?scp=85071622997&partnerID=8YFLogxK
U2 - 10.1002/chem.201903054
DO - 10.1002/chem.201903054
M3 - Article
AN - SCOPUS:85071622997
SN - 0947-6539
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
ER -