Decorated palladium nanoparticles on mesoporous organosilicate as an efficient catalyst for Sonogashira coupling reactio
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ORIGINAL PAPER
Decorated palladium nanoparticles on mesoporous organosilicate as an efficient catalyst for Sonogashira coupling reaction Fatemeh Mohajer1 · Ghodsi Mohammadi Ziarani1 · Alireza Badiei2 Received: 2 March 2020 / Accepted: 18 August 2020 © Iranian Chemical Society 2020
Abstract Reforming mesoporous silica was provided by the reaction of SBA‐15 with (3-aminopropyl)triethoxysilane, the product of which was treated with furfural to give SBA-propyl-imine-furan. In the next step, palladium chloride was attached to the functionalized SBA‐15, so Pd nanoparticles immobilized on the mentioned catalyst for providing an applicable catalyst to use in the Sonogashira cross-coupling reaction. The high stability and performance of functionalized heterogeneous hybrid catalyst of Pd@SBA-Pr-imine-furan in overall were highly essential. The nano-structured Pd@SBA-Pr-imine-furan catalyst was studied for Sonogashira cross-coupling reaction by phenylacetylene and various aryl halides under reflux conditions with a small amount of catalyst. In comparison with the earlier reports, this paper offered several benefits such as short reaction times, high yields of products, catalyst stability, quick recovery, and catalytic activity for at least seven continuous runs. Graphic abstract
Keywords Functionalization of SBA‐15 · Palladium nanoparticles · Pd@SBA-Pr-imine-furan · Sonogashira cross-coupling reaction · Furfural, heterogeneous catalyst · Decorated mesoporous silica
Introduction Electronic supplementary material The online version of this article (https://doi.org/10.1007/s13738-020-02044-4) contains supplementary material, which is available to authorized users. * Ghodsi Mohammadi Ziarani [email protected] 1
Department of Chemistry, Faculty of Physics and Chemistry, University of Alzahra, Tehran, Iran
School of Chemistry, College of Science, University of Tehran, Tehran, Iran
2
The application of the metal nanoparticles in the synthesized catalyst [1], particularly in organic production, has received much attention [2]. As a result, palladium nanoparticles (Pd NPs) have received much consideration to be sustained on the two-dimensional hexagonal structure of SBA‐15 [3, 4]. The mesoporous of SBA‐15 is full of siloxy groups; therefore, this hydrophilic structure could decrease the transportation of hydrophobic compounds, which increases the
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reaction time [5]. Thus, composite porous structures such as SBA‐15 anchored with ligands containing organic groups create the hydrophobic and hydrothermally steady structures and give them better catalytic activities in applying for organic synthesis [6]. Hence, the stability of the functionalized or decorated mesoporous silica was highly crucial in aqueous media [7, 8]. Sonogashira cross-coupling reaction was to connect the C–C bond among aryl halides and aryl alkynes, which leads to building C(sp2)-C(sp) bonds as an essential reaction in the organic synthesis [9]. The products of these reactions have extensively used for the synthesis
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