Palladium nanoparticles supported on Smopex® metal scavengers as catalyst for carbonylative Sonogashira reactions: Synthesis of α,β-alkynyl ketones

Aronica, Laura Antonella; Caporusso, Anna Maria; Tuci, Giulia; Evangelisti, Claudio; Manzoli, Maela; Botavina, Maria; Martra, Gianmario

doi:10.1016/j.apcata.2014.04.029

Cited by 23 publications

(12 citation statements)

References 59 publications

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“…The co‐condensation of palladium and copper metals together with mesitylene and 1‐hexene solvents was carried out in a static MVS reactor, equipped with two alumina‐coated tungsten crucibles that allowed evaporating independently the two metals. 150 mg of Pd and 60 mg of Cu were co‐condensed with a mixture of 1‐hexene (30 mL) and mesitylene (30 mL) under high vacuum (10 −5 mBar) on the cooled wall (−196 °C) of a glass MVS reactor chamber for one hour.…”

Section: Methodsmentioning

confidence: 99%

“…The co-condensation of palladium and copper metals together with mesitylene and 1-hexene solvents was carried out in as tatic MVS reactor, [55,56] equipped with two alumina-coated tungsten crucibles that allowed evaporating independently the two metals. 150 mg of Pd and 60 mg of Cu were co-condensed with am ixture of 1-hexene (30 mL) and mesitylene (30 mL) under high vacuum (10 À5 mBar) on the cooled wall (À196 8C) of ag lass MVS reactor chamber for one hour.T he Cu/Pd nanoparticles solution (24 mL) was added to am esitylene (20 mL) suspension of the support (4 g) (PVPy,A ldrich product, poly-4-vinylpyridine 2% cross-linked with divinylbenzene, particle size = 60 mesh, d = 0.45 gm À3 )u nder argon atmosphere.…”

Section: Experimental Section Cupd Bimetallic Catalyst Preparationmentioning

confidence: 99%

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Characterization of a Poly‐4‐Vinylpyridine‐Supported CuPd Bimetallic Catalyst for Sonogashira Coupling Reactions

et al. 2017

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CuPd bimetallic solvated metal atoms (SMA) synthesized by metal vapor synthesis (MVS) technique and supported on poly-4-vinylpyridine (PVPy) resin, showed significantly higher catalytic activity in Sonogashira-type carbon-carbon coupling reactions than the corresponding monometallic Cu and Pd systems as well as their physical mixture. The analysis of the bimetallic catalyst combining transmission electron microscopy techniques and X-ray absorption fine structure (XAFS) spectroscopy revealed the presence of small Pd nanoparticles (d =2.5 nm) while the analysis of the X-ray absorption data, at the Cu K-edge suggests the formation of thin and incomplete Cu oxide layers around the Pd-rich cores.

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Section: Methodsmentioning

confidence: 99%

Section: Experimental Section Cupd Bimetallic Catalyst Preparationmentioning

confidence: 99%

Characterization of a Poly‐4‐Vinylpyridine‐Supported CuPd Bimetallic Catalyst for Sonogashira Coupling Reactions

et al. 2017

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“…In one such study, palladium nanoparticles supported on Smopex metal scavengers as catalysts have been used to synthesize 3.1. 162 Gold and palladium combined for the Sonogashira coupling have also been used. 163,164 Instead of following the literature methods, CuI and PhCl2(PPh3)2 catalysts together were used at RT and the product was obtained with 91% yield.…”

Section: Synthesis Of Control Phenylacetylene Armsmentioning

confidence: 99%

Supramolecular BODIPY Dye Architectures for Advanced Light Harvesting and Energy Transfer Applications

Yousaf¹

2022

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Shape-persistent phenylacetylene macrocycles have been explored in a number of optoelectronic and light-harvesting applications, including two-photon absorption. Likewise, BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes) dyes have also been extensively used in material applications, owing to their tunable, intense absorption and sharp emission spectra exhibiting high quantum yields. Combining these two architectures, this thesis presents a derivative where a BODIPY is contained orthogonally within the phenylacetylene-macrocycle. This structure was inspired by photosystem II antennae complexes where energy is obsorbed by antennae complexes and funneled down to a reaction centre. Specifically, this family of molecules uses the phenylacetylene macrocycle to harvest the light and transfer it to the BODIPY core, and this has been observed by examining the fluorescence emission from the BODIPY (Figure 1). This novel dye design if coupled to a donor (D) and acceptor (A) capable of anchoring to TiO2 could be modified to become a π-spacer (i.e. D-π-A motif) for dye-sensitized solar cells resulting in panchromatic absorption, and ultimately more efficient devices.

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“…Pd NPs supported on Smopex ® -111 and Smopex ® -2 obtained through the metal vapor synthesis (MVS) technique. The versatility and fe of this synthetic approach in depositing size-controlled Pd NPs onto a wide r supports, including organic polymers, have been previously established [93][94][95][96][97][98][99][100].…”

Section: Introductionmentioning

confidence: 99%

Palladium Nanoparticles Supported on Smopex-234® as Valuable Catalysts for the Synthesis of Heterocycles

2021

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Supported catalysts are important tools for developing green-economy-based processes. Palladium nanoparticles (NPs) that are immobilized on two fibers developed as metal scavengers (i.e., Smopex®-234 and Smopex®-111, 1% w/w) have been prepared and tested in copper-free cyclocarbonylative Sonogashira reactions. Their catalytic activity has been compared with that of a homogeneous catalyst (i.e., PdCl2(PPh3)2). Pd/Smopex®-234 showed high activity and selectivity in the synthesis of functionalized heterocycles, such as phthalans and isochromans, even when working with a very low amount of palladium (0.2–0.5 mol%). The extension of Pd/Smopex®-234 promoted cyclocarbonylative reactions to propargyl and homopropargyl amides afforded the corresponding isoindoline and dihydrobenzazepine derivatives. A preliminary test on Pd NPs leaching into the solution (1.7 × 10−3 mg) seems to indicate that, at the end of the reaction, almost all of the active metal is present on the fiber surface.

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Palladium nanoparticles supported on Smopex® metal scavengers as catalyst for carbonylative Sonogashira reactions: Synthesis of α,β-alkynyl ketones

Cited by 23 publications

References 59 publications

Characterization of a Poly‐4‐Vinylpyridine‐Supported CuPd Bimetallic Catalyst for Sonogashira Coupling Reactions

Characterization of a Poly‐4‐Vinylpyridine‐Supported CuPd Bimetallic Catalyst for Sonogashira Coupling Reactions

Supramolecular BODIPY Dye Architectures for Advanced Light Harvesting and Energy Transfer Applications

Palladium Nanoparticles Supported on Smopex-234® as Valuable Catalysts for the Synthesis of Heterocycles

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