Deep Eutectic Solvents as Reaction Media for the Palladium-Catalysed C−S Bond Formation: Scope and Mechanistic Studies

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Title: Deep Eutectic Solvents as Reaction Media for the Palladium-Catalysed C−S Bond Formation: Scope and Mechanistic Studies
Authors: Marset, Xavier | Guillena, Gabriela | 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: Green chemistry | Multicomponent reactions | Palladium | Solvent effects | Sulfur
Knowledge Area: Química Orgánica
Issue Date: 4-Aug-2017
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: Chemistry - A European Journal. 2017, 23(44): 10522-10526. doi:10.1002/chem.201702892
Abstract: A unique jigsaw catalytic system based on deep eutectic solvents and palladium nanoparticles where C−S bonds are formed from aryl boronic acids and sodium metabisulfite, is introduced. The functionalization step is compatible with a broad spectrum of reagents such as nucleophiles, electrophiles or radical scavengers. This versatile approach allows the formation of different types of products in an environmentally friendly medium by selecting the components of the reaction, which engage one with another as pieces in a jigsaw. This simple procedure avoids the use of toxic volatile organic solvents allowing the formation of complex molecules in a one-pot reaction under mild conditions. Despite the fact that only 1 mol % of metal loading is used, the recyclability of the catalytic system is possible. Kinetic experiments were performed and the reaction order for all reagents, catalyst and ligand was determined. The obtained results were compared to palladium nanocrystals of different known shapes in order to shed some light on the properties of the catalyst.
Sponsor: This work was supported by the University of Alicante (UAUSTI16-10, VIGROB-173), and the Spanish Ministerio de Economía, Industria y Competitividad (CTQ2015-66624-P). X.M. thanks Generalitat Valenciana (ACIF/2016/057) for fellowship.
ISSN: 0947-6539 (Print) | 1521-3765 (Online)
DOI: 10.1002/chem.201702892
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version:
Appears in Collections:INV - CESO - Artículos de Revistas
INV - MATCAT - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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