Cyanation of aryl bromides with K4[Fe(CN)6] using polydopamine supported Pd nanoparticle catalysis: formation of magnetite during the reaction

Gazdag, Tamás; Kunfi, Attila; London, Gábor

doi:10.1007/s11144-018-1478-x

Cited by 5 publications

(3 citation statements)

References 82 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Palladium nanoparticles anchored by polydopamine (PDA) as catalyst for the synthesis of aryl nitriles was disclosed by Gazdag et al 59 Initially, it was noted that under the optimised condition (10 mg Pd/PDA, 0.125 mmol K 4 [Fe(CN) 6 ], 0.5 mmol Na 2 CO 3 in NMP at 140 °C) the yields were favourable only for electron-deficient aryl halides, other substrates reacted less effectively (Scheme 25). But, the addition of tetrabutyl ammonium bromide (TBAB), improved the efficiency of the reaction and rendered moderate to good yields.…”

Section: Introductionmentioning

confidence: 99%

Recent advances and prospects in the palladium-catalyzed cyanation of aryl halides

et al. 2020

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Recent advances and prospects in the palladium-catalyzed cyanation of aryl halides

et al. 2020

View full text Add to dashboard Cite

show abstract

“…London et al. have disclosed their results about the cyanation of aryl bromides with K 4 [Fe(CN) 6 ] induced by PDA‐based palladium preparations . Three catalysts, namely 3.3 % Pd 0 ‐PDA (methanol solution, 1–3 nm Pd particles), 13.47 % Pd 0 ‐PDA (water/acetone solution, 10–20 nm) and 3.53 % Pd 0 ‐PDA/Fe 3 O 4 (aqueous solution, 5–8 nm) were prepared.…”

Section: Organic Synthesismentioning

confidence: 99%

Polydopamine – its Prolific Use as Catalyst and Support Material

Molnár

2020

ChemCatChem

View full text Add to dashboard Cite

Polydopamine is a mussel-inspired functional material with a unique ability to form surface coatings. It is a green, environmentally benign product available very easily for a multitude of varied applications. This review attempts to collect useful information with respect to polydopamine-based catalytic studies with the use of polydopamine and modified polydopamine preparations loaded with varied catalytically active species including metal ions and metal particles. Major sections are about the use of polydopamine as catalyst material, utilization of immobilized enzymes, removal of toxic materials, results in organic synthesis, and fuel cell applications. A few examples of chiral catalysis and results of recycling studies are also treated. Data collected and analyzed indicate the importance and high potential of polydopamine-based catalysts in sustainable chemistry. of subunits attacked by an immobilized cyclohexeneamine (5) was suggested to be the transition state of CÀ C bond formation.Edouard et al. prepared catalyst 0.29 % PDA/PU by depositing PDA onto polyurethane foam (PU, 180 � 20 mg, 8 cm 3 ) and used it for the reduction of methylene blue (MB) with NaBH 4 . [48] Activities decreased gradually with repeated uses from 100 % to 35 % in run 11 but partial reactivation was achieved upon keeping the sample at 67°C for 8 h (55 % dropping below 10 % in run 13). Exposure to air at room temperature for six days proved to be somewhat more beneficial (90 % conversion in run 14 decreasing to 48 % in run 18). In a recent study they fabricated two oxidized PDA/PU samples and then loaded them with NaBH 4 . [49] One made by the usual method (dopamine/Tris, rt, 12 h, in air; sample PDA O2 PU), whereas the other was made by treating PU in a mixture of dopamine, NaOAc, and NaIO 4 (pH 5, rt, 24 h). The sample was dried (67°C) and washed thoroughly with water (PDA NaIO4 PU). Both products were dipped into an aqueous solution of NaBH 4 (0.1 M, 10 min) to afford boron contents of 2.37 and 2.11 wt%. The catalysts tested in the degradation of MB showed high activities with efficiencies of 97 % and 98 %, respectively (NaBH 4 /MB molar ratio 40, 177 mg and 209 mg catalysts, 25 min). During five reuses, the pH of the reaction medium increased because of boron loss (0.78 wt% and 0.81 wt%). The activity of PDA NaIO4 PU decreased to 89 % in run five. However, dipping the used sample into a 0.1 M NaBH 4 solution restored the original efficiency of 98 %. This, however, was only a temporary remedy, since a low efficiency of 60 % was measured in run 10. PDA was suggested by the authors to act as a redox mediator to prevent the hydrolysis/oxidation of immobilized borohydride.This formula (5) should be moved up and placed before the paragraph starting with "Edouard et al…"The Zuo group used PDA particles (avg. diameter 240 nm) to induce the reduction of MB and rhodamine B (RhB) with NaBH 4 . [50] Quinone moieties of PDA were assumed to channel electrons from NaBH 4 to the dyes. Indeed, PDA oxidized with NaIO 4 exhibited increased degradatio...

show abstract

“…Traditional methods for synthesis of aryl nitriles include Rosenmund-von Braun [29,30] and Sandmeyer [31][32][33][34][35] reactions which have drawbacks of using stoichiometric CuCN at harsh reaction conditions. To overcome these disadvantages, nowadays nucleophilic cyanation of aryl halides was performed using transition metals such as Pd [36][37][38][39][40][41][42][43][44][45][46][47][48][49][50], Ni [51] and Cu [52,53] under efficient conditions. Among the different solids for preparation of recyclable catalysts, organic polymers [54] having unique properties such as easy preparation steps, tunable hydrophilic-hydrophobic character and high loading of desired functional group are excellent materials for depositing metal nanoparticles [55].…”

Section: Introductionmentioning

confidence: 99%

Hyperbranched polymer immobilized palladium nanoparticles as an efficient and reusable catalyst for cyanation of aryl halides and reduction of nitroarenes

Shojafar

Sansano

Mikhaylov

et al. 2022

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

Cyanation of aryl bromides with K4[Fe(CN)6] using polydopamine supported Pd nanoparticle catalysis: formation of magnetite during the reaction

Cited by 5 publications

References 82 publications

Recent advances and prospects in the palladium-catalyzed cyanation of aryl halides

Recent advances and prospects in the palladium-catalyzed cyanation of aryl halides

Polydopamine – its Prolific Use as Catalyst and Support Material

Hyperbranched polymer immobilized palladium nanoparticles as an efficient and reusable catalyst for cyanation of aryl halides and reduction of nitroarenes

Contact Info

Product

Resources

About