Palladium nanoparticles stabilised by PTA derivatives in glycerol: Synthesis and catalysis in a green wet phase

Chahdoura, Faouzi; Favier, Isabelle; Pradel, Christian; Mallet‐Ladeira, Sonia; Gómez, Montserrat

doi:10.1016/j.catcom.2014.10.004

Cited by 24 publications

(28 citation statements)

References 24 publications

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“…67 Neither of these two references describe the use of inert atmosphere to carry out the syntheses. In our group, we were interested in the synthesis of metal-based NPs for applications in catalysis (couplings, hydrogenations, hydrodehalogenations, carbonylations… including tandem processes), in neat glycerol under base-free conditions, using molecular hydrogen as reducing agent, with the aim of avoiding any transformation of the solvent during the synthesis; besides palladium, NiNPs, 71 Cu 2 O NPs, 72 and CuNPs 73 were also prepared following this strategy at 100 ammonium derivatives at 60º C. 76 The as-prepared PdNPs were fully characterized, specifically in solution by XPS and Electron Microscopy techniques thanks to the negligible vapor pressure of glycerol ( Figure 9). hydrogen pressure using different types of stabilizers (top).…”

Section: Glycerol and Other Polyolsmentioning

confidence: 99%

“…TEM images recorded in glycerol for some of these PdNPs (bottom). 71,74,76 The as-prepared PdNPs were analyzed by (HR)TEM showing the formation of highly dispersed small nanoparticles; EDS analyses evidenced the presence of the corresponding stabilizer on the isolated nanoparticles. With the aim of checking the coordination of TPPTS at the metallic surface in glycerol, the synthesis and 31 P NMR monitoring of TPPTS-stabilized PdNPs was carried out at NMR tube scale ( Figure 10).…”

Section: Glycerol and Other Polyolsmentioning

confidence: 99%

“…187 An analogous nanocatalyst generated from [PdCl 2 (COD)] as metal precursor and stabilized with benzyl substituted 1,3,5-triaza-7-phosphoadamantane (PTA, Pd/L ratio = 1:1) in glycerol furnished PdNPs with a mean diameter of 3.2 ± 0.8 nm. 76 This catalyst was tested for the hydrogenation of E-4-phenylbut-3-en-2-one and was recycled up to ten times without loss of activity (Scheme 9). Notably, the size of the PdPTA NPs was smaller after the tenth run, which could be explained due to an inter-particle reorganization under the catalytic conditions in glycerol.…”

Section: Scheme 6 Hydrogenation Of Styrene Derivatives Alkynes and mentioning

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: Glycerol and Other Polyolsmentioning

confidence: 99%

Section: Scheme 6 Hydrogenation Of Styrene Derivatives Alkynes and mentioning

confidence: 99%

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

2019

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“…The water-solubility of 1,3,5-triaza-7-phosphaadamantane (PTA), its diverse mode of coordination, ease of functionalization and modification have made this compound a ligand of choice in coordination chemistry [1,2,3], catalysis [4,5,6,7,8,9,10,11,12] and bioinorganic chemistry [13,14]. N-Functionalization is the simplest modification of PTA; it leaves the cage structure and the P-coordinating ability intact and affords a series of cationic species with tunable properties in terms of hydrophilicity and reactivity.…”

Section: Introductionmentioning

confidence: 99%

Pentafluorophenyl Platinum(II) Complexes of PTA and Its N-Allyl and N-Benzyl Derivatives: Synthesis, Characterization and Biological Activity

Sgarbossa

Śliwińska-Hill

ilva³

et al. 2019

Materials

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From the well-known 1,3,5-triaza-phosphaadamantane (PTA, 1a), the novel N-allyl and N-benzyl tetrafuoroborate salts 1-allyl-1-azonia-3,5-diaza-7-phosphaadamantane (APTA(BF4), 1b) and 1-benzyl-1-azonia-3,5-diaza-7-phosphaadamantane (BzPTA(BF4), 1c) were obtained. These phosphines were then allowed to react with (Pt(μ-Cl)(C6F5)(tht))2 (tht = tetrahydrothiophene) affording the water soluble Pt(II) complexes trans-(PtCl(C6F5)(PTA)2) (2a) and its bis-cationic congeners trans-(PtCl(C6F5)(APTA)2)(BF4)2 (2b) and trans-(PtCl(C6F5)(BzPTA)2)(BF4)2 (2c). The compounds were fully characterized by multinuclear NMR, ESI-MS, elemental analysis and (for 2a) also by single crystal X-ray diffraction, which proved the trans configuration of the phosphine ligands. Furthermore, in order to evaluate the cytotoxic activities of all complexes the normal human dermal fibroblast (NHDF) cell culture were used. The antineoplastic activity of the investigated compounds was checked against the human lung carcinoma (A549), epithelioid cervix carcinoma (HeLa) and breast adenocarcinoma (MCF-7) cell cultures. Interactions between the complexes and human serum albumin (HSA) using fluorescence spectroscopy and circular dichroism spectroscopy (CD) were also investigated.

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“…Moreover, β‐substituted carbonyl compounds are the backbone of active biomolecules, such as enokipodine B (fungal biomarker) or paroxetine (antidepressant) . Synthetic methods used for the preparation of β‐arylketones are usually based on a coupling between methyl vinyl ketone (MVK) and various aryl reagents in the presence of palladium catalysts . Further functionalization, leading to appropriate β‐diarylketones, can be performed using synthetic tools that form a new carbon–carbon bond: the Heck reaction or the reductive Heck reaction (conjugate addition) .…”

Section: Introductionmentioning

confidence: 99%

Ligand‐free palladium‐catalyzed tandem pathways for the synthesis of 4,4‐diarylbutanones and 4,4‐diaryl‐3‐butenones under microwave conditions

Wirwis

Trzeciak

2019

Applied Organom Chemis

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Two efficient Pd‐catalyzed tandem pathways for the synthesis of 4,4‐diaryl‐2‐butanones and 4,4‐diaryl‐3‐buten‐2‐ones were elaborated. The first step in both procedures was the Heck coupling of methyl vinyl ketone (MVK) and various aryl iodides leading to 4‐aryl‐3‐buten‐2‐one with the yield of up to 92% in 1 hr. The second step performed with the same catalyst and a new portion of aryl iodide in the presence K2CO3 as a base produced 4,4‐diaryl‐3‐buten‐2‐ones in high yield. Reaction selectivity changed completely to saturated 4,4‐diaryl‐2‐butanones, reductive Heck products, when a tertiary amine was used instead of K2CO3. Due to the application of microwave irradiation (MW), the desired products were obtained in high yield in a short time (4 hr), using 0.5 mol% of the Pd (OAc)2 catalyst without additional ligands.

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Palladium nanoparticles stabilised by PTA derivatives in glycerol: Synthesis and catalysis in a green wet phase

Cited by 24 publications

References 24 publications

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

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

Pentafluorophenyl Platinum(II) Complexes of PTA and Its N-Allyl and N-Benzyl Derivatives: Synthesis, Characterization and Biological Activity

Ligand‐free palladium‐catalyzed tandem pathways for the synthesis of 4,4‐diarylbutanones and 4,4‐diaryl‐3‐butenones under microwave conditions

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