Palladium nanoparticles stabilised by cinchona-based alkaloids in glycerol: efficient catalysts for surface assisted processes

Reina, Antonio; Pradel, Christian; Martin, Erika; Teuma, Emmanuelle; Gómez, Montserrat

doi:10.1039/c6ra19230k

Cited by 26 publications

(40 citation statements)

References 71 publications

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“…In the absence of molecular hydrogen, the reaction With the aim of modifying the coordination mode of the ligand at the metal surface, cinchonabased alkaloids were also used as stabilizers ( Figure 9). 79 In contrast to the strong interactions between P-donor ligands and metal surface, 80 mainly by -dative Pd-P bonds, cinchona ligands can interact with the surface through both N-quinoline  bonding or by  interaction with the quinoline aromatic ring. 81,82 Using quinidine as stabilizer, small (1.…”

Section: Glycerol and Other Polyolsmentioning

confidence: 99%

“…76 More recently cinchona based alkaloids were also used as PdNPs stabilizers in glycerol. 79 The best active catalytic system was obtained starting from Pd The PdNPs stabilized by quinidine were applied in the hydrogenation reaction of various alkenes and alkynes (Scheme 13). 79 It is noteworthy to mention that in the case of 1-dodecene, only 1%…”

Section: Scheme 9 Hydrogenation Of E-4-phenylbut-3-en-2-one and Coummentioning

confidence: 99%

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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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Section: Glycerol and Other Polyolsmentioning

confidence: 99%

Section: Scheme 9 Hydrogenation Of E-4-phenylbut-3-en-2-one and Coummentioning

confidence: 99%

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

2019

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“…Although catalytic glycerol solutions are good pseudo-immobilization medium for batch mode hydrogenations, 32,33 we could not find appropriate conditions to use it a simple tubular reactor. Despite working at Table 1).…”

Section: Tubular Tri-phasic Millifluidic Reactorsmentioning

confidence: 99%

“…S1). Some reproducibility issues were observed, mainly due to the aggregation of nanoparticles, involving fouling of the channels and consequently triggering the stop of the pump.PdPVP exhibited a high activity (91% conversion; Entry 1,Table 2),while PdQN and PdTPPTS were practically inactive at high temperature (Entries 2 and 3,Table 2), in contrast to the remarkable activity exhibited under batch conditions 32,33. PdQN and PdTPPTS suspensions were not stable under the mechanic stress caused by the pumps, probably due to the lability of the stabilizers (QN and TPPTS) leading to the T A B L E 3 Continuous flow hydrogenation in a tube-in-tube reactor using PdPVP for the hydrogenation of C C bond f…”

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confidence: 99%

Hydrogenation reactions catalyzed by colloidal palladium nanoparticles under flow regime

et al. 2019

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A glycerol colloidal solution of palladium nanoparticles stabilized by PVP (PdPVP, mean diameter of 2.2 ± 0.8 × 10 −9 m) was employed under flow conditions for hydrogenation reactions. After optimization, we selected the tube-in-tube flow reactor as the more suitable system for this catalytic process due to its ability to regulate the addition of hydrogen. PdPVP nanoparticles were synthesized and fully characterized ((HR)-TEM, PXRD, EA, and ICP) both in glycerol solution and at solid state. The reduction of different substrates, including nitrobenzene, 4-phenylbut-3-en-2-one, and isophorone, was achieved under relatively smooth conditions (5-7 × 10 5 Pa of H 2) in short times (<600 s). Unfortunately, the reduction of 1-dodecene was not possible due to the faster isomerization reaction. The optimal effusion of hydrogen in the colloidal phase together with the catalytic efficiency of this system is noteworthy.

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“…In some cases, this methodology can affect the kinetics of the growth step and define the shape of the nanoparticles [53]. In our group, glycerol has been applied in the synthesis of metal and metal oxide nanoparticles under hydrogen atmosphere, precluding its reductant behaviour; glycerol acts as liquid support by the efficient immobilization of MNPs [54][55][56][57]. Contrary to monometallic nanoparticles, BMNPs prepared in alcohol medium are less common.…”

Section: Alcoholsmentioning

confidence: 99%

Bimetallic Nanoparticles in Alternative Solvents for Catalytic Purposes

et al. 2017

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Bimetallic nanoparticles represent attractive catalytic systems thanks to the synergy between both partners at the atomic level, mainly induced by electronic effects which in turn are associated with the corresponding structures (alloy, core-shell, hetero-dimer). This type of engineered material can trigger changes in the kinetics of catalyzed processes by variations on the electrophilicity/nucleophilicity of the metal centers involved and also promote cooperative effects to foster organic transformations, including multi-component and multi-step processes. Solvents become a crucial factor in the conception of catalytic processes, not only due to their environmental impact, but also because they can preserve the bimetallic structure during the catalytic reaction and therefore increase the catalyst lifetime. In this frame, the present review focuses on the recent works described in the literature concerning the synthesis of bimetallic nanoparticles in non-conventional solvents, i.e., other than common volatile compounds, for catalytic applications.

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Palladium nanoparticles stabilised by cinchona-based alkaloids in glycerol: efficient catalysts for surface assisted processes

Abstract: Cinchona-based alkaloids led to well-dispersed palladium nanoparticles in neat glycerol, leading to efficient eco-friendly catalytic phases in hydrogenations and hydrodehalogenations.

Cited by 26 publications

References 71 publications

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

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

Hydrogenation reactions catalyzed by colloidal palladium nanoparticles under flow regime

Bimetallic Nanoparticles in Alternative Solvents for Catalytic Purposes

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