Palladium Based-Polysaccharide Hydrogels as Catalysts in the Suzuki Cross-Coupling Reaction

Levy‐Ontman, Oshrat; Blum, D.; Golden, Remi; Pierschel, Eric; Leviev, Sivan; Wolfson, Adi

doi:10.1007/s10904-019-01221-0

Cited by 14 publications

(11 citation statements)

References 79 publications

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“…Based on our previous work, iota (i) carrageenan was selected as the support for the heterogeneous system [38][39][40][41][42][43][44]. With this support, the reaction with i-Pd(OAc) 2 (TPPTS) 2 was superior to that with i-PdCl 2 (TPPTS) 2 (Table 1, entries 7 and 8).…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we also proposed a simple and straightforward procedure to immobilize palladium complexes on various renewable polysaccharides by using sodium triphenylphosphine trisulfonate (TPPTS) as ligand and anchor. The new heterogeneous catalysts were successfully used in Suzuki cross-coupling [38][39][40][41][42] and Heck coupling and in the transfer hydrogenation of olefins [43,44].…”

Section: Introductionmentioning

confidence: 99%

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Green Procedure for Aerobic Oxidation of Benzylic Alcohols with Palladium Supported on Iota-Carrageenan in Ethanol

2021

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The search for selective heterogeneous catalysts for the aerobic oxidation of alcohols to ketones and aldehydes has drawn much attention in the last decade. To that end, different palladium-based catalysts have been proposed that use various organic and inorganic supports. In addition, supports that originate from a biological and renewable source that is also nontoxic and biodegradable were found to be superior. We heterogenized palladium chloride or acetate complexes with triphenylphosphine trisulfonate on iota-carrageenan xerogel by simple mixing of the complex and the polysaccharide in water. The resulting polysaccharide-catalyst mixture then underwent deep freeze and lyophilization, after which the catalyst was characterized by TEM, XPS and SEM-EDS and tested in aerobic oxidation. The new heterogeneous catalysts were successfully used for the first time in the aerobic oxidation of benzylic alcohols. Moreover, they were easily removed from the reaction mixture and recycled, yielding an increase in activity with each subsequent reuse. As determined by TEM and XPS, the reduction in palladium and the formation of nanoparticles during the reaction in ethanol yielded more active species and, therefore, higher conversion rates. A SEM-EDS analysis indicated that the palladium was thoroughly dispersed in the xerogel catalysts. Moreover, the xerogel catalyst was observed to undergo a structural change during the reaction. To conclude, the new heterogeneous catalyst was prepared by a simple and straightforward method that used a non-toxic, renewable and biodegradable support to yield an active, selective and recyclable heterogeneous system.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Green Procedure for Aerobic Oxidation of Benzylic Alcohols with Palladium Supported on Iota-Carrageenan in Ethanol

2021

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“…In another catalyst-synthesis method, palladium-based TPPTS complexes were immobilized in hydrogel beads [118]. Bead-preparation performance was tested with two different methods that involved dropping the complex and various polysaccharide solutions into (1) an aqueous or ethanol solution of 0.5 M calcium chloride or (2) an aqueous solution of chitosan.…”

Section: Immobilization Of Palladium Via Other Methodsmentioning

confidence: 99%

Recent Developments in the Immobilization of Palladium Complexes on Renewable Polysaccharides for Suzuki–Miyaura Cross-Coupling of Halobenzenes and Phenylboronic Acids

Wolfson

Levy‐Ontman

2020

Catalysts

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Polysaccharides derived from natural sources exhibit unique structures and functional groups, which have recently garnered them increased attention for their potential applicability as supports for metal catalysts. Renewable polysaccharide matrices were employed as supports for palladium complexes, with or without previous modification of the support, and were used in Suzuki cross-coupling of halobenzenes and phenylboronic acid derivatives. In this review, recent developments in the immobilization of palladium-based complexes are reported, including descriptions of the preparation procedures and catalytic activity of each system. In addition, the effects of the nature of the polymeric support and of the reaction conditions on catalytic performance are discussed.

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“…We recently heterogenized Pd(OAc) 2 (TPPTS) 2 and PdCl 2 (TPPTS) 2 (TPPTS = sodium triphenylphosphine trisulfonate ligand) on various renewable polysaccharide supports. The new catalysts were successfully employed in Suzuki cross-coupling, Heck coupling and olefin transfer-hydrogenation, using different solvents [16][17][18][19][20]. The palladium complexes that were immobilized on iota Carrageenan (i) were the most producible compared to other polysaccharide-based systems.…”

Section: Introductionmentioning

confidence: 99%

The Effect of Alcohol on Palladium Nanoparticles in i-Pd(OAc)2(TPPTS)2 for Aerobic Oxidation of Benzyl Alcohol

Levy‐Ontman

Stamker

Wolfson

2021

Metals

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In the heterogeneous catalyst i-Pd(OAc)2(TPPTS)2, Pd(II) was reduced to Pd(0) by using different alcohol solvents, and the catalyst’s activity was studied in the aerobic oxidation of benzyl alcohol. We studied the effects of the impregnation time in ethanol as a solvent and the use of various alcoholic solvents on the size of palladium nanoparticles. We found that the reduction of palladium by the various alcohols yielded palladium nanoparticles that were active in the aerobic oxidation of benzyl alcohol. As determined by DLS, TEM, and zeta potential analyses, both the impregnation time in ethanol and the type of alcohol used were observed to affect nanoparticle formation, particle size distribution, and agglomeration, as well as the conversion rate. The palladium nanoparticles’ hydrodynamic diameter sizes obtained during the 24 h of impregnation time were in the range of 10–200 nm. However, following 24 h of impregnation in ethanol the nanoparticles tended to form aggregates. The conversion rates of all the primary alcohols were similar, while for secondary alcohol, in which the hydrogen of the hydroxyl is less acidic and there is steric hindrance, the conversion was the lowest. Performing the oxidation using the solvent 1-propanol yielded smaller nanoparticles with narrower distributions in comparison to the reaction that was observed when using the ethanol solvent. On the other hand, the relatively high particle size distribution in 1-hexanol yielded agglomerates.

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Palladium Based-Polysaccharide Hydrogels as Catalysts in the Suzuki Cross-Coupling Reaction

Cited by 14 publications

References 79 publications

Green Procedure for Aerobic Oxidation of Benzylic Alcohols with Palladium Supported on Iota-Carrageenan in Ethanol

Green Procedure for Aerobic Oxidation of Benzylic Alcohols with Palladium Supported on Iota-Carrageenan in Ethanol

Recent Developments in the Immobilization of Palladium Complexes on Renewable Polysaccharides for Suzuki–Miyaura Cross-Coupling of Halobenzenes and Phenylboronic Acids

The Effect of Alcohol on Palladium Nanoparticles in i-Pd(OAc)2(TPPTS)2 for Aerobic Oxidation of Benzyl Alcohol

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