Palladium nanocatalysts in glycerol: Tuning the reactivity by effect of the stabilizer

Reina, Antonio; Serrano‐Maldonado, Alejandro; Teuma, Emmanuelle; Martin, Erika; Gómez, Montserrat

doi:10.1016/j.catcom.2017.10.004

Cited by 16 publications

(24 citation statements)

References 31 publications

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“…Palladium nanoparticle‐based catalysts play a pivotal role in H 2 ‐based reactions, such as hydrodehalogenations of haloarenes and the reduction of unsaturated substrates, including oxidized nitrogen derivatives, especially for the production of anilines at industrial scale . This versatile reactivity offers great potential towards contaminated water/soil remediation via degradation of pollutants and environmentally friendly processes by means of selective catalytic reduction approaches precluding NO x emissions .…”

Section: Introductionsupporting

confidence: 79%

“…Since the reuse of the these high‐value metal particles is a major concern from economic and environmental point of view, different approaches to prepare reusable PdNPs have been reported in the literature, such as their immobilization in liquid phases, e. g . ionic liquids, water and polyols, as well as on different solid supports, e. g . mesoporous silica, zeolites, clays, polymers, metal‐organic frameworks or carbon‐based materials .…”

Section: Introductionmentioning

confidence: 99%

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Tetraalkylammonium Functionalized Hydrochars as Efficient Supports for Palladium Nanocatalysts

et al. 2020

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With the aim of preparing bio-sourced supports with enhanced properties in catalysis, we devised an original strategy allowing the immobilization of metal nanoparticles. Thus, size-controlled hydrochars with a high degree of hydroxyl functionalities, from both neat sucrose or modified with acrylic acid (10 wt.%), were derivatized with ether linkers containing ammonium groups. These non-porous carbon-based materials were used as suitable supports for the immobilization of palladium nanoparticles. The catalytic materials were synthesized by reduction of Pd(OAc) 2 to Pd(0) under H 2 atmosphere in the presence of the corresponding hydrochar, and fully characterized by standard methods. Among the different hydrochar-supported palladium materials, those functionalized with tetraalkylammonium groups afforded heterogeneous catalysts, exhibiting high activity in hydrogenations of different types of substrates (alkynes, alkenes, and carbonyl and nitro derivatives). The most efficient catalyst was recycled up to ten runs without loss of catalytic behavior, in agreement with the unchanged composite materials after catalysis (Transmission Electron Microscopy (TEM) analyses) and the lack of metal leaching in the extracted organic products (no palladium detected by Inductively Coupled Plasma-Atomic Emission Spectrometry (ICP-AES)); these systems exhibited enhanced recyclability properties as compared to commercial Pd/C catalyst.

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Section: Introductionsupporting

confidence: 79%

Section: Introductionmentioning

confidence: 99%

Tetraalkylammonium Functionalized Hydrochars as Efficient Supports for Palladium Nanocatalysts

et al. 2020

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“…The kinetically stabilized colloidal solutions with TPPTS showed excellent catalytic properties towards facilitating cross-coupling reactions and prolonged activity upon recycling preserving its selectivity. 74,187,235 The literature reports on ligand-free Suzuki-Miyaura cross-coupling reactions under aerobic conditions attire great attention, as the presence of O 2 has thus far been deleterious towards the cross-coupling reaction. For instance, Liu and co-workers report ligand-free in situ generated nanocatalysts to work under aerobic conditions in PEG400 at room temperature for the coupling of aryl chlorides and boronic acids.…”

Section: C(sp 2 )-C(sp 2 ) Heck-mizoroki Cross-couplingmentioning

confidence: 99%

Palladium Nanoparticles in Polyols: Synthesis, Catalytic Couplings, and Hydrogenations

2019

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Alcohols, in particular polyols, are well-known for the synthesis of metal nanoparticles often acting as reducing agents, solvents, and stabilizers. Given not only their structural flexibility depending on the number of OH functions and their inherent H bonding interactions, but also the wide range of polyol molecular weights readily available, different physico-chemical properties (boiling point, polarity, viscosity) could be exploited towards the synthesis of well-defined nanomaterials. In particular, the relevance of the supramolecular structure of polyols has a fundamental impact on the formation of metal nanoparticles thereby favoring the dispersion of the nanoclusters. In the field of the metal-based nanocatalysis, palladium occupies a privileged position mainly due to its remarkable versatility in terms of reactivity representing a foremost tool in synthesis. In this review, we describe the controlled synthesis of Pd-based nanoparticles in polyol medium focusing on the progress in terms of tailoring size, morphology, structure, and surface state. Moreover, we discuss the use of 4.2. C(sp)-C(sp 2) Sonogashira cross-coupling 4.3. C(sp 2)-C(sp 2) Hiyama-Denmark cross-coupling 4.4. C(sp 2)-C(sp 2) Heck-Mizoroki cross-coupling 4.5. C(sp 2)-C(sp 2 /sp 3) Suzuki-Miyaura cross-coupling 4.5.1. In PEG and glycerol media 4.5.2. Solid-supported nanocatalysts 4.6. C(sp 2)-C(sp 2)-C(sp 2) Carbonylative Suzuki cross-coupling 4.7. C(sp 2)-C(sp 2) Ullmann-type homo-coupling 4.8. Miscellaneous: SiN and C-N amination reactions 5. Conclusions and outlook

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“…[31][32][33] Hiyama coupling have been performed in -valerolactone, 34 and more recently in glycerol, although to the best of our knowledge only one report of this coupling reaction have been published in this medium so far. 35 In this case, 2 mol % of Pd (0) nanoparticles preformed from Pd(OAc)2 and a phosphine ligand, were used as catalyst for the reaction. Only 6 biaryl products were obtained, showing uncontrolled selectivity towards homocoupling by-products, which are difficult to separate from the corresponding cross-coupling products, increasing the negative impact on the sustainability of the whole process (Fig 1).…”

Section: Introductionmentioning

confidence: 99%

NCN–Pincer–Pd Complex as Catalyst for the Hiyama Reaction in Biomass-Derived Solvents

Marset

Gea

Guillena

et al. 2018

ACS Sustainable Chem. Eng.

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A NCN-pincer-Pd complex have been synthetized and applied to Hiyama-type cross-coupling reactions between aryl halides and different types of organosilanes using neoteric solvents. This report constitutes a green approach to cross-coupling reactions since the reagents employed are stable and non-toxic. The solvents used (Deep Eutectic Solvents based on choline chloride or glycerol) are also biodegradable, non-toxic, non-flammable and biorenewable. Furthermore, the catalytic system can be recycled, allowing to perform the reaction for at least three cycles without adding more catalyst or solvent, increasing the value of the process from an economical and environmental point of view. The effect of these solvents on the catalytic activity has been studied. Finally, a gram-scale reaction has also been tested affording biaryl products in high yields and purity by a simple liquid-liquid extraction, without the need of aqueous work-up or chromatographic steps, proving the applicability of this approach in a sustainable industrial scale.

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Palladium nanocatalysts in glycerol: Tuning the reactivity by effect of the stabilizer

Cited by 16 publications

References 31 publications

Tetraalkylammonium Functionalized Hydrochars as Efficient Supports for Palladium Nanocatalysts

Tetraalkylammonium Functionalized Hydrochars as Efficient Supports for Palladium Nanocatalysts

Palladium Nanoparticles in Polyols: Synthesis, Catalytic Couplings, and Hydrogenations

NCN–Pincer–Pd Complex as Catalyst for the Hiyama Reaction in Biomass-Derived Solvents

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