On the peculiar recycling properties of charcoal-supported palladium oxide nanoparticles in Sonogashira reactions

Rossy, Cybille; Majimel, Jérôme; Delapierre, Mona Tréguer; Fouquet, Éric; Felpin, François‐Xavier

doi:10.1016/j.apcata.2014.05.019

Cited by 20 publications

(10 citation statements)

References 43 publications

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“…Furthermore, the transition metal based cross‐coupling such as Suzuki‐Miyaura, Heck, Sonogashira reactions are important for the development of C−C bonds. These coupling reactions have attracted a lot of interest in the area of material science, medicinal and natural product synthesis and are applied in pharmaceutical and fine chemical industries .…”

Section: Introductionmentioning

confidence: 99%

Catalytic Selective Hydrogenation and Cross Coupling Reaction Using Polyvinylpyrrolidone‐Capped Nickel Nanoparticles

Bathla

Pal

2018

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This study signifies the size‐dependent catalytic activity of Ni‐nanocatalyst for the selective hydrogenation of cinnamaldehyde and Suzuki‐Miyaura cross‐coupling reaction. A series of polyvinylpyrrolidone capped nickel nanoparticles (NPs) with variation in their size are synthesized by polyol method. The morphological studies revealed that average size of Ni‐NPs (Ni‐NP1, Ni‐NP2, and Ni‐NP3) lies in the range of 10–12, 7–9, and 3–5 nm respectively. The optical measurements showed a significant blue shift in the absorption spectra for Ni‐NPs with decreasing particle size. The magnetic hysteresis loop revealed that the remanent magnetization (MR) decreases and coercivity (HC) increases with the decrease in particle size demonstrating a distinct size effect. The Ni‐NP3 was observed to possess higher surface area (79 m2g−1) and efficient activity for the selective hydrogenation of cinnamaldehyde to cinnamyl alcohol and also in the biphenyl formation via C−C cross‐coupling reaction relative to Ni‐NP1, Ni‐NP2, and commercially available Raney Ni.

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Section: Introductionmentioning

confidence: 99%

Catalytic Selective Hydrogenation and Cross Coupling Reaction Using Polyvinylpyrrolidone‐Capped Nickel Nanoparticles

Bathla

Pal

2018

ChemistrySelect

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“…The authors found that Pd 0 nanoparticles are stable to metal leaching throughout the reaction. Moreover, it has been reported that the Suzuki coupling reaction between bromobenzene and phenylboronic acid in EtOH/H 2 O is solely facilitated by nanosized Pd clusters, which were stable to metal leaching 10. Despite these facts, the possibility for the leached Pd to be the active species could not be ruled out in view of the many reports supporting such a role 14.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, several research groups have reported that PdO, PdO hydrate, and Pd 0 nanoparticles generated by the reduction of PdO act as catalysts for the Suzuki coupling reaction at room temperature 9. PdO has been applied to other types of coupling reactions 10. Moreover, Joucla et al synthesized ( E )‐stilbenes from chloroiodobenzenes using sequential one‐pot Suzuki–Miyaura and Heck reactions using Pd/C or Pd/SiO 2 11.…”

Section: Introductionmentioning

confidence: 99%

Suzuki Coupling Reactions Catalyzed by PdO Dispersed on Dealuminated Y Zeolite in Air under Ambient Conditions

et al. 2015

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Suzuki coupling reactions are performed using PdO loaded on dealuminated Y (USY) zeolite. The reaction between bromobenzene and phenylboronic acid is complete in 15 min at room temperature in air, with a turnover number of 1300. The reaction can be repeated at least five times by using 1 wt % Pd. Inductively coupled plasma analysis does not reveal the dissolution of Pd from products, even if the reaction is repeated up to four times. Pd K-edge extended X-ray absorption fine structure analysis reveals the presence of molecular-like PdO and a mixture of Pd(0) -PdO before and after the reaction, respectively. This is probably because Pd stabilized by Al sites is present at the II sites of the Y-type zeolite, as estimated using first-principles calculations. Conversely, Pd species change to PdO clusters after repeated reactions in air using the thermally treated sample.

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“…Moreover, incomplete reduction to Pd 0 may occur if Pd II precursors are used as a source of Pd . Even in the presence of an excess of reducing agent, the amount of unreacted Pd II may exceed 25 % ––. Thus, such catalysts may contain a combination of Pd II /Pd 0 centers, the ratio of which is difficult to control.…”

Section: Figurementioning

confidence: 99%

Rapid “Mix‐and‐Stir” Preparation of Well‐Defined Palladium on Carbon Catalysts for Efficient Practical Use

et al. 2017

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A facile direct deposition approach for the preparation of recyclable Pd/C catalysts simply by stirring a solution of tris(dibenzylideneacetone)dipalladium(0) with a suitable carbon material was evaluated. An extraordinarily rapid catalyst preparation procedure (<5 min) under mild conditions and its excellent performance in cross‐coupling and hydrogenation reactions were demonstrated. The key point for catalyst design is the direct deposition of Pd0 centers onto the highly accessible surface area and the avoidance of ill‐defined PdII/Pd0 states.

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On the peculiar recycling properties of charcoal-supported palladium oxide nanoparticles in Sonogashira reactions

Cited by 20 publications

References 43 publications

Catalytic Selective Hydrogenation and Cross Coupling Reaction Using Polyvinylpyrrolidone‐Capped Nickel Nanoparticles

Catalytic Selective Hydrogenation and Cross Coupling Reaction Using Polyvinylpyrrolidone‐Capped Nickel Nanoparticles

Suzuki Coupling Reactions Catalyzed by PdO Dispersed on Dealuminated Y Zeolite in Air under Ambient Conditions

Rapid “Mix‐and‐Stir” Preparation of Well‐Defined Palladium on Carbon Catalysts for Efficient Practical Use

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