Special Issue "Solid-Supported Reagents in Palladium-Catalyzed Transformations"

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Metal Catalysis".

Deadline for manuscript submissions: closed (31 May 2018)

Special Issue Editor

Guest Editor
Prof. Dr. Rafael Chinchilla

Department of Organic Chemistry, University of Alicante, PO Box 99, 03080 Alicante, Spain
Website | E-Mail
Interests: supported reagents; palladium-catalyzed reactions; asymmetric synthesis; organocatalysis

Special Issue Information

Dear Colleagues,

Palladium is arguably the most versatile and most-widely applied metal in catalytic transformations. Thus, palladium-mediated processes have become essential tools in the preparation of natural products, polymers, agrochemicals, pharmaceuticals, industrial commodities, and so on. This far-reaching scope is due to palladium’s ability to participate in catalytic transformations, as well as its high functional group tolerance. Palladium can be used to conduct uncountable transformations with organic molecules. In fact, there are many well-known name reactions that feature this metal, such as the Heck, Suzuki, Stille, Sonogashira and Buchwald-Hartwig cross-couplings, the Wacker process or the Tsuji-Trost allylation. In addition, palladium catalysis also enables hydrogenation, hydrogenolysis, carbonylation, oxidation, carbon-carbon and carbon-heteroatom bond formation, or cycloisomerization reactions. Domino processes, where multiple palladium-promoted transformations are carried out in a single operation, are also a powerful application of palladium catalysis. Palladium-catalyzed procedures often take place under mild conditions, affording high yields, with excellent levels of selectivity. All these processes mainly take place under homogeneous conditions, something that represents a serious drawback for large-scale applications, considering the problem associated with the recovery of the often-expensive palladium catalyst after product formation.

Immobilization of the palladium catalyst on a solid and insoluble support can drive to advantages related to its easier isolation and recycling compared to the cases of soluble counterparts, or its use in continuous flow chemistry. In the last years, many examples have been reported on the use of palladium species, such as complexes or nanoparticles, anchored to a solid support as recyclable catalysts. Thus, numerous solid supports have been employed for anchoring the palladium species, such as polymers, silica-related materials, metal oxides, carbon-based structures, metal organic frameworks, etc. However, despite these developments, plenty of work is still ahead to achieve supported catalytic palladium systems successfully applicable to all reactions suitable to being carried out under homogeneous conditions above mentioned, paying special attention to aspects, such as their high reactivity and recyclability.  

This Special Issue of Catalysts aims to provide a diverse overview of the latest developments in the preparation of solid-supported palladium species and their use as catalysts in all these interesting chemical transformations.

Prof. Dr. Rafael Chinchilla
Guest Editor

Manuscript Submission Information

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Keywords

  • Palladium catalysis
  • Solid supported catalysts
  • Heterogeneous catalysis
  • Palladium nanoparticles

Published Papers (4 papers)

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Research

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Open AccessArticle Improvement Effect of Ni to Pd-Ni/SBA-15 Catalyst for Selective Hydrogenation of Cinnamaldehyde to Hydrocinnamaldehyde
Catalysts 2018, 8(5), 200; https://doi.org/10.3390/catal8050200
Received: 12 March 2018 / Revised: 17 April 2018 / Accepted: 27 April 2018 / Published: 11 May 2018
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Abstract
A series of Pd-Ni bimetallic catalysts supported on SBA-15 (0.2%Pd-x%Ni/SBA-15, x = 0.4, 0.7, and 1.2) were prepared through the impregnation method combined with the NaBH4 reduction method. X-ray diffraction (XRD), N2 adsorption-desorption, X-ray photoemission spectroscopy (XPS) and transmission electron microscope
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A series of Pd-Ni bimetallic catalysts supported on SBA-15 (0.2%Pd-x%Ni/SBA-15, x = 0.4, 0.7, and 1.2) were prepared through the impregnation method combined with the NaBH4 reduction method. X-ray diffraction (XRD), N2 adsorption-desorption, X-ray photoemission spectroscopy (XPS) and transmission electron microscope (TEM) were used to characterize the prepared catalysts. All the synthesized catalysts were evaluated for the liquid-phase hydrogenation of cinnamaldehyde (CAL). The addition of Ni obviously enhanced the CAL conversion and selectivity of C=C hydrogenation to hydrocinnamaldehyde (HALD) over the 0.2%Pd-x%Ni/SBA-15 catalysts. Meanwhile, 0.2%Pd-1.2%Ni/SBA-15 showed the best performance with 96.3% conversion and 87.8% selectivity toward HALD. This improvement was attributed to the synergistic effect between the Pd and Ni nanoparticles, enhancing the dispersion of Pd metal particles and increasing the content of surface Pd0 species. In addition, the influences of a few reaction factors including H2 pressure, reaction temperature, and reaction time were studied over 0.2%Pd-1.2%Ni/SBA-15. Full article
(This article belongs to the Special Issue Solid-Supported Reagents in Palladium-Catalyzed Transformations)
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Open AccessFeature PaperArticle Polystyrene-Supported Acyclic Diaminocarbene Palladium Complexes in Sonogashira Cross-Coupling: Stability vs. Catalytic Activity
Catalysts 2018, 8(4), 141; https://doi.org/10.3390/catal8040141
Received: 9 March 2018 / Revised: 22 March 2018 / Accepted: 28 March 2018 / Published: 2 April 2018
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Abstract
Two types of immobilized on the amino-functionalized polystyrene-supported acyclic diaminocarbene palladium complexes (ADC-PdII) are investigated under Sonogashira cross-coupling conditions. Depending on substituents in the diaminocarbene fragment immobilized ADC-PdII, systems are found to have different catalytic activity and stability regarding
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Two types of immobilized on the amino-functionalized polystyrene-supported acyclic diaminocarbene palladium complexes (ADC-PdII) are investigated under Sonogashira cross-coupling conditions. Depending on substituents in the diaminocarbene fragment immobilized ADC-PdII, systems are found to have different catalytic activity and stability regarding Pd-leaching. PdII-diaminocarbenes possessing protons at both nitrogen atoms smoothly decompose into Pd0-containing species providing a catalytic “cocktail system” with high activity and ability to reuse within nine runs. Polymer-supported palladium (II) complex bearing NBn–Ccarbene–NH-moiety exhibits greater stability while noticeably lower activity under Sonogashira cross-coupling. Four molecular ADC-PdII complexes are also synthesized and investigated with the aim of confirming proposed base-promoted pathway of ADC-PdII conversion through carbodiimide into an active Pd0 forms. Full article
(This article belongs to the Special Issue Solid-Supported Reagents in Palladium-Catalyzed Transformations)
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Open AccessArticle Heavy Oil Upgrading and Enhanced Recovery in a Steam Injection Process Assisted by NiO- and PdO-Functionalized SiO2 Nanoparticulated Catalysts
Catalysts 2018, 8(4), 132; https://doi.org/10.3390/catal8040132
Received: 27 February 2018 / Revised: 22 March 2018 / Accepted: 22 March 2018 / Published: 29 March 2018
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Abstract
This work aims to investigate the effect of active catalytic nanoparticles on the improvement of the efficiency in recovery of a continuous steam injection process. Catalytic nanoparticles were selected through batch-adsorption experiments and the subsequent evaluation of the temperature for catalytic steam gasification
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This work aims to investigate the effect of active catalytic nanoparticles on the improvement of the efficiency in recovery of a continuous steam injection process. Catalytic nanoparticles were selected through batch-adsorption experiments and the subsequent evaluation of the temperature for catalytic steam gasification in a thermogravimetric analyzer. A nanoparticulated SiO2 support was functionalized with 1.0 wt % of NiO and PdO nanocrystals, respectively, to improve the catalytic activity of the nanoparticles. Oil recovery was evaluated using a sand pack in steam injection scenarios in the absence and presence of a 500 mg/L SiNi1Pd1 nanoparticles-based nanofluid. The displacement test was carried out by constructing the base curves with water injection followed by steam injection in the absence and presence of the prepared treatment. The oil recovery increased 56% after steam injection with nanoparticles in comparison with the steam injection in the absence of the catalysts. The API gravity increases from 7.2° to 12.1°. Changes in the asphaltenes fraction corroborated the catalytic effect of the nanoparticles by reducing the asphaltenes content and the 620 °C+ residue 40% and 47%, respectively. Also, rheological measurements showed that the viscosity decreased by up to 85% (one order of magnitude) after the nanofluid treatment during the steam injection process. Full article
(This article belongs to the Special Issue Solid-Supported Reagents in Palladium-Catalyzed Transformations)
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Review

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Open AccessReview Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments
Catalysts 2018, 8(5), 202; https://doi.org/10.3390/catal8050202
Received: 19 April 2018 / Revised: 8 May 2018 / Accepted: 9 May 2018 / Published: 11 May 2018
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Abstract
The Sonogashira cross-coupling reaction is the most frequently employed synthetic procedure for the preparation of arylated alkynes, which are important conjugated compounds with multiple applications. Despite of their rather high price, this reaction is usually catalyzed by palladium species, making the recovery and
[...] Read more.
The Sonogashira cross-coupling reaction is the most frequently employed synthetic procedure for the preparation of arylated alkynes, which are important conjugated compounds with multiple applications. Despite of their rather high price, this reaction is usually catalyzed by palladium species, making the recovery and reuse of the catalyst an interesting topic, mainly for industrial purposes. Easy recycle can be achieved anchoring the palladium catalyst to a separable support. This review shows recent developments in the use of palladium species anchored to different solid supports as recoverable catalysts for Sonogashira cross-coupling reactions. Full article
(This article belongs to the Special Issue Solid-Supported Reagents in Palladium-Catalyzed Transformations)
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