Hydroxy- and alkoxycarbonylation of aryl iodides catalyzed by polymer-supported palladium

Beletskaya, I. P.; Ganina, Olga G.

doi:10.1007/s11144-009-0099-9

Cited by 5 publications

(7 citation statements)

References 9 publications

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“…Previously, we developed a catalytic system of PdNPs supported on a soluble statistical copolymer of N ‐vinylimidazole with N ‐vinylcaprolacam (30 %; PVI‐PVCL), which revealed high activity and recyclability in the Heck reaction,12 the cyanation of aryl halides,13 and the carbonylation of aryl iodides 14. Polymer PVI‐PVCL successfully models natural enzymes on the basis of peptide macromolecules 15.…”

Section: Resultsmentioning

confidence: 99%

Palladium Nanoparticles Supported on Poly(N‐vinyl‐ imidazole‐co‐N‐vinylcaprolactam) as an Effective Recyclable Catalyst for the Suzuki Reaction

2014

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A recyclable and effective polymer‐immobilized ligandless palladium catalyst for the Suzuki reaction has been investigated. Palladium nanoparticles are formed in situ and stabilized by poly(N‐vinylimidazole‐co‐N‐vinylcaprolactam). A series of aryl bromides have been studied in the reaction with phenylboronic acid under mild conditions with water–alcohol systems as a solvent that complies with “Green Chemistry” demands. The catalyst can be recycled eight times without appreciable loss in activity and a low degree of palladium leaching. Kinetic studies reveal unusual behavior of the reaction; this can be explained on the basis of the observation of changes to the sizes of the particles during recycling, as determined by TEM results. The suggested mechanism of the reaction is in accordance with the concept of the role of leaching in the process.

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Section: Resultsmentioning

confidence: 99%

Palladium Nanoparticles Supported on Poly(N‐vinyl‐ imidazole‐co‐N‐vinylcaprolactam) as an Effective Recyclable Catalyst for the Suzuki Reaction

2014

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“…Beletskaya and Ganina reported palladium nanoparticles immobilised on poly(N-vinylimidazole-co-N-vinylcaprolactam) (PdNPs/PVI-PVC) in methanol for the alkoxycarbonylation of aryl iodides (Scheme 40). 42 The PdNPs/PVI-PVC catalyst could be recycled several times without loss of activity.…”

Section: Heterogeneous Palladium Catalysed Alkoxycarbonylation Reacti...mentioning

confidence: 99%

Recent developments in palladium catalysed carbonylation reactions

2014

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“…Use of the Pd-PS-PEO catalyst in hydroxycarbonylation reactions gave excellent results. The hydroxycarbonylation of meta - and para -iodobenzoic acids was carried out in water at room temperature using PdNPs micellar catalyst and KOH as a base [ 23 ]. Both reactions proceeded with full conversion to give quantitative yields of phthalic acids after 24 h. For 3-iodobenzoic acid, the catalyst was recycled 11 times, with full isolation of the product in the first five cycles and spectroscopic determination of yields in the final six cycles ( Figure 7 ).…”

Section: Palladium Nanoparticlesmentioning

confidence: 99%

“…The efficient hydroxycarbonylation of aryl iodides catalyzed by Pd-PS-PEO-CPC prompted us to carry out alkoxycarbonylation in methanol using PdCl 2 -PVI-PVC as a pre-catalyst [ 23 ]. The study of reaction conditions has shown that the best result can be obtained with 1 mol% Pd/5 mol% PVI-PVC at 55 ºC and 1 atm CO using Et 3 N as a base ( Table 3 , entry 12).…”

Section: Palladium Nanoparticlesmentioning

confidence: 99%

Recyclable Nanostructured Catalytic Systems in Modern Environmentally Friendly Organic Synthesis

Beletskaya

Tyurin

2010

Molecules

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Modern chemical synthesis makes heavy use of different types of catalytic systems: homogeneous, heterogeneous and nano-sized. The latter – nano-sized catalysts – have given rise in the 21st century to a rapidly developing area of research encompassing several prospects and opportunities for new technologies. Catalytic reactions ensure high regio- and stereoselectivity of chemical transformations, as well as better yields and milder reaction conditions. In recent years several novel catalytic systems were developed for selective formation of carbon-heteroatom and carbon-carbon bonds. This review presents the achievements of our team in our studies on various types of catalysts containing metal nanoparticles: palladium-containing diblock copolymer micelles; soluble palladium-containing polymers; metallides on a support; polymeric metal salts and oxides; and, in addition, metal-free organic catalysts based on soluble polymers acting as nanoreactors. Representative examples are given and discussed in light of possible applications to solve important problems in modern organic synthesis.

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Hydroxy- and alkoxycarbonylation of aryl iodides catalyzed by polymer-supported palladium

Abstract: The efficient carbonylation of aryl iodides catalyzed by palladium immobilized on polymers in water or methanol under very mild conditions is reported. The catalyst can be recycled several times without loss of activity.

Cited by 5 publications

References 9 publications

Palladium Nanoparticles Supported on Poly(N‐vinyl‐ imidazole‐co‐N‐vinylcaprolactam) as an Effective Recyclable Catalyst for the Suzuki Reaction

Palladium Nanoparticles Supported on Poly(N‐vinyl‐ imidazole‐co‐N‐vinylcaprolactam) as an Effective Recyclable Catalyst for the Suzuki Reaction

Recent developments in palladium catalysed carbonylation reactions

Recyclable Nanostructured Catalytic Systems in Modern Environmentally Friendly Organic Synthesis

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