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Please use this identifier to cite or link to this item: http://hdl.handle.net/10481/48288

Title: Suzuki-Miyaura C-C Coupling Reactions Catalyzed by Supported Pd Nanoparticles for the Preparation of Fluorinated Biphenyl Derivatives
Authors: Erami, Roghayeh Sadeghi
Díaz-García, Diana
Prashar, Sanjiv
Rodríguez-Diéguez, Antonio
Fajardo, Mariano
Amirnasr, Mehdi
Gómez-Ruiz, Santiago
Issue Date: 28-Feb-2017
Abstract: Heterogeneous recyclable catalysts in Suzuki-Miyaura C-C coupling reactions are of great interest in green chemistry as reusable alternatives to homogeneous Pd complexes. Considering the interesting properties of fluorinated compounds for the pharmaceutical industry, as precursors of novel materials, and also as components of liquid crystalline media, this present study describes the preparation of different fluorinated biphenyl derivatives by Suzuki-Miyaura coupling reactions catalyzed by a heterogeneous system (G-COOH-Pd-10) based on Pd nanoparticles supported onto COOH-modified graphene. The catalytic activity of the hybrid material G-COOH-Pd-10 has been tested in Suzuki-Miyaura C–C coupling reactions observing excellent versatility and good conversion rates in the reactions of phenylboronic acid, 4-vinylphenylboronic acid, 4-carboxyphenylboronic acid, and 4-fluorophenylboronic acid with 1-bromo-4-fluorobenzene. In addition, the influence of the arylbromide has been studied by carrying out reactions of 4-fluorophenylboronic acid with 1-bromo-2-fluorobenzene, 1-bromo-3-fluorobenzene, 1-bromo-4-fluorobenzene, 2-bromo-5-fluorotoluene, and 2-bromo-4-fluorotoluene. Finally, catalyst recyclability tests show a good degree of reusability of the system based on G-COOH-Pd-10 as the decrease in catalytic activity after five consecutive catalytic cycles in the reaction of 1-bromo-4-fluorobenzene with 4-florophenylboronic acid at 48 hours of reaction is lower than 8% while in the case of reactions at three hours the recyclability of the systems is much lower.
Sponsorship: We gratefully acknowledge financial support from the Ministerio de Economía y Competitividad, Spain (Grant no. CTQ2015-66164-R). We would also like to thank Universidad Rey Juan Carlos and Banco de Santander for supporting our Research Group of Excellence QUINANOAP. We would also like to thank Isfahan University of Technology for the partial financial support of the research stay of R.S.E.
Publisher: MDPI
Keywords: Pd nanoparticles
C-C coupling
Fluorinated compounds
Graphene
Supported catalysts
Suzuki-Miyaura reactions
URI: http://hdl.handle.net/10481/48288
ISSN: 2073-4344
Citation: Erami, R.S.; et al. Suzuki-Miyaura C-C Coupling Reactions Catalyzed by Supported Pd Nanoparticles for the Preparation of Fluorinated Biphenyl Derivatives. Catalysts, 7(3): 76 (2017). [http://hdl.handle.net/10481/48288]
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