Fe3O4@SiO2/EDAC–Pd(0) as a novel and efficient inorganic/organic magnetic composite: sustainable catalyst for the benzylic C–H bond oxidation and reductive amination under mild conditions

Bhardwaj, Madhvi; Sharma, Hemant; Paul, Satya; Clark, James H.

doi:10.1039/c5nj03413b

Cited by 25 publications

(23 citation statements)

References 50 publications

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“…A layer of was incorporated over to form Fe 3 O 4 @SiO 2 NP ( 2 ) by adding tetraethylorthosilicate (TEOS) to it and stirring for 18 h 25 . Palladium nanoparticle was deposited onto the surface of Fe 3 O 4 @SiO 2 NP in situ by reducing using at low temperature Fe 3 O 4 @SiO 2 /Pd 0 NP ( 3 ) 26 . Palladium ions ( ) on the surface of Fe 3 O 4 @SiO 2 NP was sorbed by adding solution with stirring to yield NP ( 4 ).…”

Section: Resultsmentioning

confidence: 99%

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A magnetically retrievable mixed-valent Fe3O4@SiO2/Pd0/PdII nanocomposite exhibiting facile tandem Suzuki coupling/transfer hydrogenation reaction

Singh

Mishra

Sahoo

et al. 2021

Sci Rep

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Herein, we report a magnetically retrievable mixed-valent Fe3O4@SiO2/Pd0/PdIINP (5) nanocomposite system for tandem Suzuki coupling/transfer hydrogenation reaction. The nanocomposite 5 was prepared first by making a layer of $$\hbox {SiO}_{2}$$ SiO 2 on $$\hbox {Fe}_{3}\hbox {O}_{4}\hbox {NP}$$ Fe 3 O 4 NP followed by deposition of $$\hbox {Pd}^{0}$$ Pd 0 and sorption of $$\hbox {Pd}^{\mathrm{II}}$$ Pd II ions successively onto the surface of Fe3O4@SiO2NP. The nanocomposite was characterized by powder XRD, electron microscopy (SEM-EDS and TEM-EDS) and XPS spectroscopy techniques. The mixed-valent $$\hbox {Pd}^{0}/\hbox {Pd}^{\mathrm{II}}$$ Pd 0 / Pd II present onto the surface of nanocomposite 5 was confirmed by XPS technique. Interestingly, the mixed-valent nanocomposite Fe3O4@SiO2/Pd0/PdIINP (5) exhibited tandem Suzuki coupling/transfer hydrogenation reaction during the reaction of aryl bromide with aryl boronic acid (90% of C). The nanocomposite 5 displayed much better reactivity as compared to the monovalent Fe3O4@SiO2/Pd0NP (3) (25% of C) and Fe3O4@SiO2/PdIINP (4) (15% of C) nanocomposites. Further, because of the presence of magnetic $$\hbox {Fe}_{3}\hbox {O}_{4}$$ Fe 3 O 4 , the nanocomposite displayed its facile separation from the reaction mixture and reused at least for five catalytic cycles.

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Section: Resultsmentioning

confidence: 99%

“…The peaks at 334.78 eV and 340.16 eV; 337.73 eV and 342.85 eV correspond to and of metallic palladium ( ) and oxidized palladium [ : PdO or (Fig. 3 b) 26 , 31 , 33 , 39 – 46 . This confirms presence of mixed-valent palladium ( and ) in nanocomposite 5 .…”

Section: Resultsmentioning

confidence: 99%

A magnetically retrievable mixed-valent Fe3O4@SiO2/Pd0/PdII nanocomposite exhibiting facile tandem Suzuki coupling/transfer hydrogenation reaction

Singh

Mishra

Sahoo

et al. 2021

Sci Rep

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“…Another example of DRA catalysed by Pd NPs supported onto magnetite based nanocomposites has been reported by Paul’s group, that synthesized in 2016 Pd(0) nanoparticles dispersed onto ethylene diamine functionalized inorganic/organic magnetic composite [ 66 ]. In details, Fe 3 O 4 nanoparticles were prepared with the co-precipitation method, and were coated with silica spheres with the sol-gel process.…”

Section: Metal-catalyzed One-pot Reductive Amination Reactionmentioning

confidence: 99%

Metal-based Heterogeneous Catalysts for One-Pot Synthesis of Secondary Anilines from Nitroarenes and Aldehydes

et al. 2021

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Recently, N-substituted anilines have been the object of increasing research interest in the field of organic chemistry due to their role as key intermediates for the synthesis of important compounds such as polymers, dyes, drugs, agrochemicals and pharmaceutical products. Among the various methods reported in literature for the formation of C–N bonds to access secondary anilines, the one-pot reductive amination of aldehydes with nitroarenes is the most interesting procedure, because it allows to obtain diverse N-substituted aryl amines by simple reduction of nitro compounds followed by condensation with aldehydes and subsequent reduction of the imine intermediates. These kinds of tandem reactions are generally catalyzed by transition metal-based catalysts, mainly potentially reusable metal nanoparticles. The rapid growth in the last years in the field of metal-based heterogeneous catalysts for the one-pot reductive amination of aldehydes with nitroarenes demands for a review on the state of the art with a special emphasis on the different kinds of metals used as catalysts and their recyclability features.

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“…In the transformations of carbonyl compounds with nitroaromatic compounds to secondary amines several monometallic supported catalysts have been applied, such as Pd, [46][47][48] Pt, [30] Au modified by NH 2 groups, [49] Ni supported on H-ZSM-5 zeolite (Ni/H-mZSM-5) [50] and bimetallic noble metal catalysts. [11,51,52] To overcome the high price of noble metal catalysts, cheaper transition metal catalysts have also been applied. [23,28,50,53] Typically reactions are carried out in the temperature range of 25-190°C- [52,53] under 1-50 bar hydrogen pressure [28,52] or with other hydrogen sources including in-situ generated hydrogen from the water gas shift reaction, [23,54] decomposition of formic acid [53,55,56] and sodium borohydride.…”

Section: Introductionmentioning

confidence: 99%

One-pot amination of aldehydes and ketones over heterogeneous catalysts for production of secondary amines

2021

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This review summarizes the recent studies on the synthesis of secondary amines by one-pot amination of aldehydes and ketones over heterogeneous catalysts. Amines are widely applied as the key intermediates in chemical industry for the synthesis of various commodities such as agrochemicals, drugs, detergents, lubricants, food-additives and polymers. Direct catalytic reductive amination of carbonyl compounds was considered which generally includes two steps: (i) formation of imines by interactions of aldehydes or ketones with amines, and (ii) subsequent hydrogenation of imines. Synthesis of secondary amines from carbonyl compounds and amines generated in situ under reaction conditions from their progenitors, e.g., respectively, alcohols or nitro-compounds, is also discussed in detail. Recent progress in application of hydrogen sources alternative to gaseous H 2 , such as formic acid, NaBH 4 , CO and water, favored development of metal-free catalysts including solid acid catalysts. The review addresses the scope of the amination reaction with aldehydes/ketones and nitro/amine compounds of different structure, the effect of the solvent, reaction conditions and catalyst properties. In addition, catalyst regeneration and reuse, kinetic regularities and kinetic modeling with an emphasis on the continuous mode of one-pot amination have been systematically summarized and discussed. It is suggested that the future work should focus on revealing the role of the catalytically active sites addressing their acid-base properties and the correlation between catalyst properties and the reaction performance, elucidating kinetic parameters and designing feasible reactor system for further industrial implementation.

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Fe₃O₄@SiO₂/EDAC–Pd(0) as a novel and efficient inorganic/organic magnetic composite: sustainable catalyst for the benzylic C–H bond oxidation and reductive amination under mild conditions

Abstract: Magnetically recyclable ethylene diamine functionalized inorganic/organic composite, Fe3O4@SiO2/EDAC–Pd(0) for selective C–H bond oxidation and reductive amination under sustainable reaction media.

Cited by 25 publications

References 50 publications

A magnetically retrievable mixed-valent Fe3O4@SiO2/Pd0/PdII nanocomposite exhibiting facile tandem Suzuki coupling/transfer hydrogenation reaction

A magnetically retrievable mixed-valent Fe3O4@SiO2/Pd0/PdII nanocomposite exhibiting facile tandem Suzuki coupling/transfer hydrogenation reaction

Metal-based Heterogeneous Catalysts for One-Pot Synthesis of Secondary Anilines from Nitroarenes and Aldehydes

One-pot amination of aldehydes and ketones over heterogeneous catalysts for production of secondary amines

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