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Solid-Supported Reagents in Palladium-Catalyzed Transformations

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

Deadline for manuscript submissions: closed (31 May 2018) | Viewed by 24172

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Special Issue Editor

Prof. Dr. Rafael Chinchilla

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Guest Editor

Department of Organic Chemistry, Faculty of Sciences, and Institute of Organic Synthesis (ISO), University of Alicante, P.O. Box 99, 03080 Alicante, Spain
Interests: asymmetric synthesis; organocatalysis; solid-supported reagents; palladium-catalyzed reactions
Special Issues, Collections and Topics in MDPI journals

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

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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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16 pages, 3232 KiB

Open AccessArticle

Improvement Effect of Ni to Pd-Ni/SBA-15 Catalyst for Selective Hydrogenation of Cinnamaldehyde to Hydrocinnamaldehyde

by Shiying Han, Yunfei Liu, Jiang Li, Rui Li, Fulong Yuan and Yujun Zhu

Catalysts 2018, 8(5), 200; https://doi.org/10.3390/catal8050200 - 11 May 2018

Cited by 23 | Viewed by 4539

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 (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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19 pages, 9260 KiB

Open AccessFeature PaperEditor’s ChoiceArticle

Polystyrene-Supported Acyclic Diaminocarbene Palladium Complexes in Sonogashira Cross-Coupling: Stability vs. Catalytic Activity

by Vladimir N. Mikhaylov, Viktor N. Sorokoumov, Denis Martin Liakhov, Alexander G. Tskhovrebov and Irina A. Balova

Catalysts 2018, 8(4), 141; https://doi.org/10.3390/catal8040141 - 02 Apr 2018

Cited by 35 | Viewed by 5872

Abstract

Two types of immobilized on the amino-functionalized polystyrene-supported acyclic diaminocarbene palladium complexes (ADC-Pd^II) are investigated under Sonogashira cross-coupling conditions. Depending on substituents in the diaminocarbene fragment immobilized ADC-Pd^II, systems are found to have different catalytic activity and stability regarding Pd-leaching. Pd^II-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–C_carbene–NH-moiety exhibits greater stability while noticeably lower activity under Sonogashira cross-coupling. Four molecular ADC-Pd^II complexes are also synthesized and investigated with the aim of confirming proposed base-promoted pathway of ADC-Pd^II 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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14 pages, 4666 KiB

Open AccessArticle

Heavy Oil Upgrading and Enhanced Recovery in a Steam Injection Process Assisted by NiO- and PdO-Functionalized SiO₂ Nanoparticulated Catalysts

by Luisana Cardona, Daniela Arias-Madrid, Farid B. Cortés, Sergio H. Lopera and Camilo A. Franco

Catalysts 2018, 8(4), 132; https://doi.org/10.3390/catal8040132 - 29 Mar 2018

Cited by 42 | Viewed by 5388

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 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

Jump to: Research

39 pages, 13950 KiB

Open AccessReview

Solid-Supported Palladium Catalysts in Sonogashira Reactions: Recent Developments

by Diego A. Alonso, Alejandro Baeza, Rafael Chinchilla, Cecilia Gómez, Gabriela Guillena, Isidro M. Pastor and Diego J. Ramón

Catalysts 2018, 8(5), 202; https://doi.org/10.3390/catal8050202 - 11 May 2018

Cited by 50 | Viewed by 7678

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 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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