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.

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

Melchionna M.;
2019-01-01

Abstract

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.
Pubblicato
http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3765
https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201903054
File in questo prodotto:
File Dimensione Formato  
oCNT-CEJ-edited-jh.pdf

Accesso chiuso

Descrizione: Articolo principale
Tipologia: Documento in Pre-print
Licenza: Copyright Editore
Dimensione 1 MB
Formato Adobe PDF
1 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
chem.201903054.pdf

Accesso chiuso

Tipologia: Documento in Versione Editoriale
Licenza: Copyright Editore
Dimensione 1.52 MB
Formato Adobe PDF
1.52 MB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11368/2952097
Citazioni
  • ???jsp.display-item.citation.pmc??? 1
  • Scopus 13
  • ???jsp.display-item.citation.isi??? 13
social impact