Programmed Synthesis Palladium Supported on Fe3O4@C: An Efficient and Heterogeneous Recyclable Catalyst for One-Pot Reductive Amination of Aldehydes with Nitroarenes in Aqueous Reaction Medium

Zhou, Xingchun; Li, Xinzhe; Jiao, Lixin; Huo, Hongfei; Li, Rong

doi:10.1007/s10562-015-1552-1

Cited by 16 publications

(11 citation statements)

References 24 publications

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“…Isotope labeling experiments adapted from Ref. [2] Copyright permission from Elsevier Ltd. [52] (Continued) [90] (Continued) [52] (Continued) (Continued) [65] (Continued) exceeding 99% under mild conditions (Table 5, entry 23). [85] This example is beyond the scope of secondary amine synthesis, which is in the core of the current review, but could be considered as an one of the important synthesis methods.…”

Section: Figure 11mentioning

confidence: 99%

“…[52] The reaction time was also quite short over Pd-Fe 3 O 4 /SiO 2 (ethylene diamine), 2.5 h [52] in comparison to Pd/Fe 3 O 4 /C for which 8 h was required (Table 7, entry 10, Table S2, entry 10). [90] Moreover, separation and recycle was reported to be facile. Analogously Pd/Fe 3 O 4 -NH 2 /starch (Pd@Fe 3 O 4 -NH 2 -starch) catalyst with the average diameter of Pd particles of 8.4 nm was efficient in benzaldehyde amination with nitrobenzene giving 93% yield at 25°C in the ethanol-water mixture under hydrogen atmosphere already after 2 h (Table 7, entry 9, Table S2, entry 9).…”

Section: Catalyst Selectionmentioning

confidence: 99%

“…Catalyst recyclability. Several catalysts exhibited very good recyclability in amination of benzaldehyde with nitrobenzene such as Pd/polymer, [46] PdCu supported on β-cyclodextrin, [66] Pd/Fe 3 O 4 , [51] Pd supported on Fe 3 O 4 carbon composite catalyst, [90] Pd@MIL-101, [30] Pd 2 Ag 1 @MIL-101, [65] Pd/Fe 2 O 3 @C, [90] Fe 2 O 3 supported on nitrogen doped graphitic carbon composite catalyst (NGr@C). [28] Metal leaching can be a problem in the liquid phase reductive aminations, for example in HMF amination in ethanol over Pd/C, 76% of Pd was leached out from the commercial catalyst after 6 h. [67] In addition, Pd leaching occurred during HMF amination also from Pd/UiO-67 (ca.…”

Section: Molar Feed Ratiomentioning

confidence: 99%

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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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Section: Figure 11mentioning

confidence: 99%

Section: Catalyst Selectionmentioning

confidence: 99%

Section: Molar Feed Ratiomentioning

confidence: 99%

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

2021

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“…Li’s research group prepared other core–shell Fe 3 O 4 @C nanoparticles (of 160 nm in diameter) having a carbon layer coating of 10 nm in thickness onto which Pd NPs of 3–8 nm in size were homogeneously dispersed (Pd/Fe 3 O 4 @C) [ 65 ]. These nano materials represent a rare example of catalysts active for DRA performed in water.…”

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 last decade, numerous other catalytic systems were developed based on supported palladium (Sydnes et al, 2008;Sreedhar et al, 2009;Dell'anna et al, 2011;Wei et al, 2013;Zhou et al, 2015;Sharma et al, 2017), platinum (Hu et al, 2011;Cirujano et al, 2013), rhodium (Huang et al, 2015), iridium Pintado-Sierra et al, 2013;Sui et al, 2017), ruthenium (Del Pozo et al, 2012), silver (Artiukha et al, 2017), and gold (Yamane et al, 2009;Artiukha et al, 2015) nanoparticles. Heterobimetallic systems such as Pd-Ag (Li et al, 2013;Chen et al, 2015), Pd-Au (Cho et al, 2018;Yin et al, 2018), Ni-Pd (Nişanci et al, 2015), and Rh-Co (Park and Chung, 2015) were also shown to be efficient catalysts for the reductive alkylation of nitro compounds.…”

Section: Intermolecular Reductive Amination Of Aldehydes and Ketones mentioning

confidence: 99%

Catalytic Reductive Amination of Aldehydes and Ketones With Nitro Compounds: New Light on an Old Reaction

Sukhorukov

2020

Front. Chem.

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Reductive amination of carbonyl compounds with primary amines is a well-established synthetic methodology for the selective production of unsymmetrically substituted secondary and tertiary amines. From the industrial and green chemistry perspective, it is attractive to combine reductive amination with the synthesis of primary amines in a single one-pot catalytic process. In this regard, nitro compounds, which are readily available and inexpensive feedstocks, received much attention as convenient precursors to primary amines in such processes. Although the direct reductive coupling of nitro compounds with aldehydes/ketones to give secondary and tertiary amines has been known since the 1940's, due to the development of highly efficient and selective non-noble metal-based catalysts a breakthrough in this area was made in the last decade. In this short overview, recent progress in the methodology of the reductive amination with nitro compounds is summarized together with applications to the synthesis of bioactive amines and heterocycles. Remaining challenges in this field are also analyzed.

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Programmed Synthesis Palladium Supported on Fe3O4@C: An Efficient and Heterogeneous Recyclable Catalyst for One-Pot Reductive Amination of Aldehydes with Nitroarenes in Aqueous Reaction Medium

Cited by 16 publications

References 24 publications

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

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

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

Catalytic Reductive Amination of Aldehydes and Ketones With Nitro Compounds: New Light on an Old Reaction

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