Catechol-Functionalized Carbon Nanotubes as Support for Pd Nanoparticles: a Recyclable System for the Heck Reaction

Alessandro Mercadante, Vincenzo Campisciano, Anthony Morena, Laura Valentino, Valeria La Parola, Carmela Aprile, Michelangelo Gruttadauria, Francesco Giacalone

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Carbon nanotubes have been covalently functionalized with catechol moieties through the formation of the corresponding aryl radicals obtained by reacting 4-aminocatechol with isoamyl nitrite. The functionalized multiwalled carbon nanotubes have been in turn used to immobilize Pd(II) ions on its surface forming catechol-Pd complexes, which were reduced to Pd nanoparticles (NPs). The so-obtained hybrid material has been characterized by means of thermogravimetric analysis coupled with differential scanning calorimetry (TGA-DSC), X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM). This latter technique allowed to estimate the nanoparticle size (5.7±2.8 nm) whereas a palladium loading of 20.3 wt % has been found by inductively coupled plasma optical emission spectroscopy (ICP-OES). The carbon nanotube-catechol-Pd hybrid was used as catalyst in two C−C coupling reactions, namely Suzuki and Heck reactions, resulting recyclable for at least 9 times in the latter process. During the reuse Pd nanoparticles increase their dimension to 19.3±11.7 nm.

langue originaleAnglais
Numéro d'articlee202200497
journalEuropean Journal of Organic Chemistry
Les DOIs
Etat de la publicationPublié - 13 oct. 2022

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