TY - JOUR
T1 - Catechol-Functionalized Carbon Nanotubes as Support for Pd Nanoparticles
T2 - a Recyclable System for the Heck Reaction
AU - Mercadante, Alessandro
AU - Campisciano, Vincenzo
AU - Morena, Anthony
AU - Valentino, Laura
AU - La Parola, Valeria
AU - Aprile, Carmela
AU - Gruttadauria, Michelangelo
AU - Giacalone, Francesco
N1 - Funding Information:
The authors gratefully acknowledge the University of Palermo and the Italian Ministry of Education, University and Research (MIUR) for financial support through PRIN 2017 (projects no. 2017W8KNZW and 2017YJMPZN). Open Access funding provided by Università degli Studi di Palermo within the CRUI‐CARE Agreement.
Publisher Copyright:
© 2022 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH.
PY - 2022/10/13
Y1 - 2022/10/13
N2 - 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.
AB - 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.
KW - Carbon nanotubes
KW - C−C coupling reactions
KW - Heterogeneous catalysis
KW - Palladium nanoparticles
KW - Suzuki and Heck reactions
UR - http://www.scopus.com/inward/record.url?scp=85135916707&partnerID=8YFLogxK
U2 - 10.1002/ejoc.202200497
DO - 10.1002/ejoc.202200497
M3 - Article
AN - SCOPUS:85135916707
SN - 1434-193X
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
M1 - e202200497
ER -