Journal
CHEMPLUSCHEM
Volume 81, Issue 5, Pages 471-476Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cplu.201600023
Keywords
C-C coupling; heterogeneous catalysis; nanotubes; supported catalysts; supramolecular chemistry
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Funding
- University of Palermo
- P.O.R. Sicilia, Misura 3.15 Quota Regionale
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The surfaces of multi-walled carbon nanotubes (MWCNTs) were non-covalently modified using two bis-imidazolium dibromide derivatives having phenyl or pyrene groups. Due to the presence of the two pyrene groups the bis(pyren-1-ylmethylimidazolium) dibromide derivative was immobilised at a loading of about 15-16 wt%, whereas only < 3 wt% of the phenyl derivative was immobilised. The presence of the two imidazolium cations helped the immobilisation of tetrachloropalladate ions after exchange with bromide ions. Tetrachloropalladate was used as pre-catalyst in several Suzuki-Miyaura carbon-carbon cross-coupling reactions in water or water/ethanol at 50 degrees C in only 0.1 mol% and compared with the non-supported pre-catalyst. The MWCNT-supported material was used in five consecutive cycles of the Suzuki-Miyaura reaction. Recycling using phenylboronic acid and 4-bromobenzaldehyde in water/ethanol was achieved with only a minor loss in activity. HRTEM images clearly showed the presence of the bis(pyren-1-ylmethylimidazolium) derivative on the sidewalls of MWCNTs.
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