Deep Eutectic Solvent Compatible Metallic Catalysts: Cationic Pyridiniophosphine Ligands in Palladium Catalyzed Cross-Coupling Reactions

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Title: Deep Eutectic Solvent Compatible Metallic Catalysts: Cationic Pyridiniophosphine Ligands in Palladium Catalyzed Cross-Coupling Reactions
Authors: Marset, Xavier | Khoshnood, Abbas | Sotorríos, Lia | Gómez Bengoa, Enrique | Alonso, Diego A. | Ramón, Diego J.
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Cross-coupling | Green chemistry | Palladium | Phosphane ligands | Solvent effects
Knowledge Area: Química Orgánica
Issue Date: 7-Apr-2017
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: ChemCatChem. 2017, 9(7): 1269-1275. doi:10.1002/cctc.201601544
Abstract: Cationic pyridiniophosphine ligands have been synthetized in an attempt to develop a deep eutectic solvents (DESs) compatible catalytic systems. These ligands, in combination with PdCl2, have been successfully applied to different palladium-catalyzed cross coupling reactions, such as Suzuki–Miyaura, Sonogashira, or Heck couplings. While traditional palladium ligands in DES medium failed to reproduce the results obtained in VOC solvents, these cationic phosphines improved the catalytic activity of palladium as no other traditional ligand could in such a polar medium. In addition, the recyclability of these processes was studied, allowing us to reuse both, catalyst and solvent up to 5 times in Suzuki and Sonogashira reactions without a significant drop in the catalytic activity. Regarding the structure of the Pd catalysts, titration, NMR, and DFT studies have clearly demonstrated the coordination properties of the DES-compatible cationic phosphine ligands.
Sponsor: Financial support from the University of Alicante (UAUSTI16-03, UAUSTI16-10, VIGROB-173, VIGROB-285), the Spanish Ministerio de Economía, Industria y Competitividad (CTQ2015-66624-P) as well as the UPV-EHV for technical and human support provided by IZO-SGI SGIker. XM thanks MINECO (PEJ-2014-P-00290) and Generalitat Valenciana (ACIF/2016/057) for fellowships.
ISSN: 1867-3880 (Print) | 1867-3899 (Online)
DOI: 10.1002/cctc.201601544
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
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Appears in Collections:INV - MATCAT - Artículos de Revistas
INV - CESO - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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