Recent Application of Polymer Supported Metal Nanoparticles in Heck, Suzuki and Sonogashira Coupling Reactions

Karimi, Babak; Behzadnia, Hesam; Farhangi, Elham; Jafari, Ehsan; Zamani, Asghar

doi:10.2174/157017910794328538

Cited by 42 publications

(20 citation statements)

References 108 publications

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“…Less reactive aryl chlorides have not been employed much in palladium-catalyzed coupling reactions because the oxidative addition of the C-Cl bond to Pd(0) species is usually difficult. 30,31 In our catalytic system, chloroarenes coupled with phenylacetylene in the presence of tetrabutylammonium bromide (TBAB) as an additive (Table 1, entries [11][12][13][14][15]. Although the effect of TBAB in the coupling reactions is not completely clear, it has a promoting effect in the regeneration of zerovalent palladium by reductive elimination of Pd(II) compound in the presence of base.…”

Section: Resultsmentioning

confidence: 99%

“…The mixture was then purified by column chromatography over silica gel using petroleum ether/ethyl acetate or recrystallization with CHCl 3 to afford a product with high purity. The identity of the products was determined by comparison of their FT-IR, 1 H NMR, 13 C NMR, and physical data with those of the authentic samples.…”

Section: General Procedures For the Sonogashira-hagihara Coupling Reacmentioning

confidence: 99%

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Palladium nanoparticles supported on modified polystyrene resin as a polymeric catalyst for Sonogashira--Hagihara coupling reactions

Tamami¹,

Dodeji²,

Ghasemi³

2015

Turk J Chem

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Pd(0) nanoparticles supported on modified crosslinked polystyrene were synthesized and characterized.Crosslinked polystyrene was reacted with trioxane and chlorotrimethylsilane in the presence of SnCl 4 to form Merrifield resin. The Merrifield resin was then converted to polymer-bound β -aminoalcohol and subsequently to βaminophosphinite ligand. This polymeric ligand was reacted with PdCl 2 to obtain a polymeric Pd(0) complex. The TEM image of the Pd catalyst showed good dispersion of catalytic sites. The Pd catalyst exhibits excellent activity and stability in copper-free Sonogashira-Hagihara cross-coupling reactions under aerobic conditions. This protocol can be applied efficiently to the coupling reactions of chloro-as well as iodo-and bromo-arenes. The catalyst can be reused several times without any considerable decrease in its activity.

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Section: Resultsmentioning

confidence: 99%

Section: General Procedures For the Sonogashira-hagihara Coupling Reacmentioning

confidence: 99%

Palladium nanoparticles supported on modified polystyrene resin as a polymeric catalyst for Sonogashira--Hagihara coupling reactions

Tamami¹,

Dodeji²,

Ghasemi³

2015

Turk J Chem

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“…Syntheses of these nanoparticles employ a variety of Pd precursors and stabilisers. For the current study, polymeric stabilisers [14,15] are of particular interest. The polymer most commonly used to stabilize NPs is poly-(N-vinyl-2-pyrollidone) (PVP), however, many other polymers have been used as well (see, e.g., Refs.…”

Section: Nanoparticle Catalysismentioning

confidence: 99%

Halide-Enhanced Catalytic Activity of Palladium Nanoparticles Comes at the Expense of Catalyst Recovery

et al. 2017

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Abstract:In this communication, we present studies of the oxidative homocoupling of arylboronic acids catalyzed by immobilised palladium nanoparticles in aqueous solution. This reaction is of significant interest because it shares a key transmetallation step with the well-known Suzuki-Miyaura cross-coupling reaction. Additives can have significant effects on catalysis, both in terms of reaction mechanism and recovery of catalytic species, and our aim was to study the effect of added halides on catalytic efficiency and catalyst recovery. Using kinetic studies, we have shown that added halides (added as NaCl and NaBr) can increase the catalytic activity of the palladium nanoparticles more than 10-fold, allowing reactions to be completed in less than half a day at 30 • C. However, this increased activity comes at the expense of catalyst recovery. The results are in agreement with a reaction mechanism in which, under conditions involving high concentrations of chloride or bromide, palladium leaching plays an important role. Considering the evidence for analogous reactions occurring on the surface of palladium nanoparticles under different reaction conditions, we conclude that additives can exert a significant effect on the mechanism of reactions catalyzed by nanoparticles, including switching from a surface reaction to a solution reaction. The possibility of this switch in mechanism may also be the cause for the disagreement on this topic in the literature.

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“…Their applications also include removal a a Fig. 4: SEM images of (a) PS-HDODA beads (b) chloromethylated resin of hydrogen from water, nitrates from drinking water and in coupling and substitution reactions 27,28 .…”

Section: Applications Of Polymer Supported Metal Complexes Catalysismentioning

confidence: 99%

Synthesis and Applications of Nano Metallic Particles Anchored on a Novel Polymeric Resin

Varkey¹

2017

Orient. J. Chem

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Nanocatalysis is a rapidly growing research field which involves the use of nanomaterials as catalysts for both homogenous and heterogeneous catalysis. Because of the huge surface area contrasted to bulk matter nanomaterials can function as more efficient catalysts. The main challenge in applying nanoparticles in catalysis is to stabilize and control their size. This problem can be solved by incorporating metal nanoparticles in channels of solid supports. Resin supported metal nanoparticles are popular in many catalytic reactions. Crosslinked polymers are superior because of their ease of filtration and purification. But most of the resins currently using are of having poor reactivity due to their low strength. The support is not acting as a passive solid carrier and the crosslinked polymer is notably influencing the rate of the reactions carried on it. In this review polystyrene crosslinked with 1, 6 -hexanediol diacrylate (HDODA) is introduced for nanoparticle supported catalysis. The amount of crosslinking should be accurately adjusted because this has an intense effect on the reactivity of the synthesized polymer. The flexible nature and suitable swelling features of the styrene-HDODA resin will facilitate successful synthesis and the swelling property of this resin is much more compared to the resins commonly used now. The preparation, characterization and catalytic applications of functional polymers are presented.

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Recent Application of Polymer Supported Metal Nanoparticles in Heck, Suzuki and Sonogashira Coupling Reactions

Cited by 42 publications

References 108 publications

Palladium nanoparticles supported on modified polystyrene resin as a polymeric catalyst for Sonogashira--Hagihara coupling reactions

Palladium nanoparticles supported on modified polystyrene resin as a polymeric catalyst for Sonogashira--Hagihara coupling reactions

Halide-Enhanced Catalytic Activity of Palladium Nanoparticles Comes at the Expense of Catalyst Recovery

Synthesis and Applications of Nano Metallic Particles Anchored on a Novel Polymeric Resin

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