Palladium and Bimetallic Palladium–Nickel Nanoparticles Supported on Multiwalled Carbon Nanotubes: Application to Carbon–Carbon Bond-Forming Reactions in Water

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Title: Palladium and Bimetallic Palladium–Nickel Nanoparticles Supported on Multiwalled Carbon Nanotubes: Application to Carbon–Carbon Bond-Forming Reactions in Water
Authors: Ohtaka, Atsushi | Sansano, Jose M. | Nájera, Carmen | Miguel García, Izaskun | Berenguer-Murcia, Ángel | Cazorla-Amorós, Diego
Research Group/s: Síntesis Asimétrica (SINTAS) | Materiales Carbonosos y Medio Ambiente
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Departamento de Química Inorgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | Universidad de Alicante. Instituto Universitario de Materiales
Keywords: Cross-coupling | Nanoparticles | Nanotubes | Palladium | Water
Knowledge Area: Química Orgánica | Química Inorgánica
Issue Date: 15-Jun-2015
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: ChemCatChem. 2015, 7(12): 1841-1847. doi:10.1002/cctc.201500164
Abstract: Palladium and bimetallic Pd–Ni nanoparticles (NPs) protected by polyvinylpyrrolidone were prepared by the reduction-by-solvent method and deposited on multiwalled carbon nanotubes (MWCNTs). The catalytic activity of these NPs to carbon–carbon bond-forming reactions was studied by using 0.1 mol % Pd loading, at 120 °C for 1 h and water as a solvent under ligand-free conditions. The Suzuki–Miyaura reaction took place quantitatively for the cross-coupling of 4-bromoanisole with phenylboronic acid, better than those obtained with potassium phenyltrifluoroborate, with Pd50Ni50/MWCNTs as a catalyst and K2CO3 as a base and TBAB as an additive, with good recyclability during 4 cycles with some Ni leaching. The Hiyama reaction of 4-iodoanisole with trimethoxyphenylsilane, under fluoride-free conditions using 50 % aqueous NaOH solution, was performed with Pd/MWCNTs as a catalyst in 83 % yield with low recyclability. For the Mizoroki-Heck reaction 4-iodoanisole and styrene gave the corresponding 4-methoxystilbene quantitatively with Pd50Ni50/MWCNTs using K2CO3 as a base and TBAB as an additive although the recycle failed. In the case of the Sonogashira-Hagihara reaction, Pd/MWCNTs had to be used as a catalyst and pyrrolidine as a base for the coupling of 4-iodoanisole with phenylacetylene under copper-free conditions. The corresponding 4-methoxytolane was quantitatively obtained allowing the recycling of the catalyst during 3 cycles.
Sponsor: The Spanish Ministerios de Ciencia e Innovación (MICINN) and Economía y Competitividad (MINECO) (projects CTQ 2007-62771/BQU, CTQ2010-20387, CTQ2013-43446-P, Consolider Ingenio 2010, CSD2007-00006, CTQ2014-51912-REDC, CTQ2012-31762 and RyC-2009-03813 fellowship), FEDER, the Generalitat Valenciana (PROMETEO 2009/039, PROMETEOII/2014/010, and PROMETEOII/2014/017) and the University of Alicante are gratefully acknowledged for financial support.
ISSN: 1867-3880 (Print) | 1867-3899 (Online)
DOI: 10.1002/cctc.201500164
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version:
Appears in Collections:INV - SINTAS - Artículos de Revistas
INV - MCMA - Artículos de Revistas

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