Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Oxidative N-Formylation of Secondary Amines Catalyzed by Reusable Bimetallic AuPd-Fe3O4 Nanoparticles.

ABSTRACT: Bimetallic catalysts are gaining attention due to their characteristics of promoting reactivity and selectivity in catalyzed reactions. Herein, a new catalytic N-formylation of secondary amines using AuPd-Fe3O4 at room temperature is reported. Methanol was utilized as the formyl source and 1.0 atm of O2 gas served as an external oxidant. The bimetallic catalyst, consisting of Au and Pd, makes the reaction more efficient than that using each metal separately. In addition, the catalyst can be effectively recycled owing to the Fe3O4 support.

SUBMITTER: Yang S

PROVIDER: S-EPMC8400704 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Oxidative N-Formylation of Secondary Amines Catalyzed by Reusable Bimetallic AuPd-Fe3O4 Nanoparticles.

Yang Sabyuk S Cho Ahra A Cho Jin Hee JH Kim Byeong Moon BM

Nanomaterials (Basel, Switzerland) 20210818 8

Bimetallic catalysts are gaining attention due to their characteristics of promoting reactivity and selectivity in catalyzed reactions. Herein, a new catalytic N-formylation of secondary amines using AuPd-Fe3O4 at room temperature is reported. Methanol was utilized as the formyl source and 1.0 atm of O2 gas served as an external oxidant. The bimetallic catalyst, consisting of Au and Pd, makes the reaction more efficient than that using each metal separatel ...[more]

PMID: 34443931

Similar Datasets

Supported Bimetallic AuPd Nanoparticles as a Catalyst for the Selective Hydrogenation of Nitroarenes.

Project description:The solvent-free selective hydrogenation of nitrobenzene was carried out using a supported AuPd nanoparticles catalyst, prepared by the modified impregnation method (MIm), as efficient catalyst >99% yield of aniline (AN) was obtained after 15 h at 90 °C, 3 bar H₂ that can be used without any further purification or separation, therefore reducing cost and energy input. Supported AuPd nanoparticles catalyst, prepared by MIm, was found to be active and stable even after four recycle experiments, whereas the same catalyst prepared by SIm was deactivated during the recycle experiments. The most effective catalyst was tested for the chemoselective hydrogenation of 4-chloronitrobenzene (CNB) to 4-chloroaniline (CAN). The activation energy of CNB to CAN was found to be 25 kJ mol-1, while that of CNB to AN was found to be 31 kJ mol-1. Based on this, the yield of CAN was maximized (92%) by the lowering the reaction temperature to 25 °C.

| S-EPMC6165381 | biostudies-literature

Synthesis and Structural Characterization of Branched Bimetallic AuPd Nanoparticles with a Highly Tunable Optical Response.

Project description:Bimetallic nanostructures composed of gold (Au) and palladium (Pd) have garnered increased interest for their applications in heterogeneous catalysis. This study reports a simple strategy for manufacturing Au@Pd bimetallic branched nanoparticles (NPs), which offer a tunable optical response, using polyallylamine-stabilized branched AuNPs as template cores for Pd overgrowth. The palladium content can be altered by manipulating the concentration of PdCl42- and ascorbic acid (AA) that are injected, which permit an overgrowth of the Pd shell up to ca. 2 nm thick. The homogeneous distribution of Pd at the surfaces of Au NPs can be carried out regardless of their size or branching degree, which allows for an adjustment of the plasmon response in the near-infrared (NIR) spectral range. As a proof of concept, the nanoenzymatic activity of pure gold and gold-palladium NPs was compared, exploring their peroxidase-like activity in the oxidation of 3,3',5,5'-tetramethylbenzidine (TMB). The bimetallic AuPd NPs demonstrate an increase in the catalytic properties attributed to the presence of palladium at the surface of gold.

| S-EPMC10350956 | biostudies-literature

Glycolaldehyde as a Bio-Based C1 Building Block for Selective N-Formylation of Secondary Amines.

Project description:Biomass derived glycolaldehyde was employed as C1 building block for the N-formylation of secondary amines using air as oxidant. The reaction is atom economic, highly selective and proceeds under catalyst free conditions. This strategy can be used for the synthesis of cyclic and acyclic formylamines, including DMF. Mechanistic studies suggest a radical oxidation pathway.

| S-EPMC9826180 | biostudies-literature

Gold-catalyzed intermolecular Markovnikov hydroamination of allenes with secondary amines.

Project description:A cationic (CAAC)gold(I) complex promotes the addition of all types of nontertiary amines to a variety of allenes, affording allylic amines in good to excellent yields; the amino fragment always adds to the less substituted terminus of the CCC skeleton.

| S-EPMC2739117 | biostudies-literature

Stable and reusable Ni-based nanoparticles for general and selective hydrogenation of nitriles to amines.

Project description:Silica supported ultrasmall Ni-nanoparticles allow for general and selective hydrogenation of all kinds of nitriles to primary amines under mild conditions. By calcination of a template material generated from Ni(ii)nitrate and colloidal silica under air and subsequent reduction in the presence of molecular hydrogen the optimal catalyst is prepared. The prepared supported nanoparticles are stable, can be conveniently used and easily recycled. The applicability of the optimal catalyst material is shown by hydrogenation of >110 diverse aliphatic and aromatic nitriles including functionalized and industrially relevant substrates. Challenging heterocyclic nitriles, specifically cyanopyridines, provided the corresponding primary amines in good to excellent yields. The resulting amines serve as important precursors and intermediates for the preparation of numerous life science products and polymers.

| S-EPMC9491304 | biostudies-literature

Mild and Rapid Light-Driven Suzuki-Miyaura Reactions Catalyzed by AuPd Nanoparticles in Water at Room Temperature.

Project description:Organic reactions carried out in water under mild conditions are state-of-the-art in terms of environmentally benign chemical processes. In this direction, plasmonic catalysis can aid in accomplishing such tasks. In the present work, cyclodextrin-mediated AuPd bimetallic nanoparticles (NPs) were applied in room-temperature aqueous Suzuki-Miyaura reactions aiming at preparing biaryl products based on fluorene, isatin, benzimidazole and resorcinol, with yields of 77 % up to 95 %. AuPd NPs were revealed to be a physical mixture of Au and Pd particles circa 20 and 2 nm, respectively, through X-ray diffraction, dynamic light scattering, UV-Vis spectroscopy and transmission electron microscopy analyses.

| S-EPMC9716040 | biostudies-literature

N-formylation of lysine in histone proteins as a secondary modification arising from oxidative DNA damage.

Project description:The posttranslational modification of histone and other chromatin proteins has a well recognized but poorly defined role in the physiology of gene expression. With implications for interfering with these epigenetic mechanisms, we now report the existence of a relatively abundant secondary modification of chromatin proteins, the N(6)-formylation of lysine that appears to be uniquely associated with histone and other nuclear proteins. Using both radiolabeling and sensitive bioanalytical methods, we demonstrate that the formyl moiety of 3'-formylphosphate residues arising from 5'-oxidation of deoxyribose in DNA, caused by the enediyne neocarzinostatin, for example, acylate the N(6)-amino groups of lysine side chains. A liquid chromatography (LC)-tandem mass spectrometry (MS) method was developed to quantify the resulting N(6)-formyl-lysine residues, which were observed to be present in unperturbed cells and all sources of histone proteins to the extent of 0.04-0.1% of all lysines in acid-soluble chromatin proteins including histones. Cells treated with neocarzinostatin showed a clear dose-response relationship for the formation of N(6)-formyl-lysine, with this nucleosome linker-selective DNA-cleaving agent causing selective N(6)-formylation of the linker histone H1. The N(6)-formyl-lysine residue appears to represent an endogenous histone secondary modification, one that bears chemical similarity to lysine N(6)-acetylation recognized as an important determinant of gene expression in mammalian cells. The N(6)-formyl modification of lysine may interfere with the signaling functions of lysine acetylation and methylation and thus contribute to the pathophysiology of oxidative and nitrosative stress.

| S-EPMC1765477 | biostudies-literature

Reductive Oligomerization of Nitroaniline Catalyzed by Fe3O4 Spheres Decorated with Group 11 Metal Nanoparticles

Project description:The present work demonstrates a simple and sustainable

| S-EPMC9979374 | biostudies-literature

Selective N-Alkylation of Amines with DMC over Biogenic Cu-Zr Bimetallic Nanoparticles.

Project description:Herein, we report the green synthesis of copper-zirconium bimetallic nanoparticles (Cu-Zr BNPs) from aqueous solutions using Azadirachta indica leaf extract as a reducing and stabilizing agent. The CuO, ZrO2 NP, and Cu-Zr BNP samples were characterized by X-ray diffraction and Fourier transform infrared (FTIR) spectroscopy, and the morphologies of the samples were analyzed by high-resolution transmission electron microscopy (HR-TEM) with selected area electron diffraction analysis (SAED). The synthesized Cu-Zr BNPs have been employed as efficient catalysts for the selective N-methylation of aromatic and aliphatic amines with dimethyl carbonate. The effect of process conditions on the percentage conversion of benzylamine with dimethyl carbonate as a model reaction has been investigated. The Cu-Zr bimetallic nanoparticle catalytic system in a 1:2 molar ratio was able to convert amines into the corresponding N-methylated amines with a selectivity up to 91% at 180 °C in 4 h. The analysis of catalytic reusability confirmed that the reported heterogeneous catalyst can be used for five consecutive cycles without much loss in activity. Thus, the current protocol can be considered as a simpler, reproducible, and environmentally benign approach for N-methylation of amines.

| S-EPMC8210448 | biostudies-literature

Ethanol Electrooxidation at 1-2 nm AuPd Nanoparticles.

Project description:We report a systematic study of the electrocatalytic properties and stability of a series of 1-2 nm Au, Pd, and AuPd alloy nanoparticles (NPs) for the ethanol oxidation reaction (EOR). Following EOR electrocatalysis, NP sizes and compositions were characterized using aberration-corrected scanning transmission electron microscopy (ac-STEM) and energy dispersive spectroscopy (EDS). Two main findings emerge from this study. First, alloyed AuPd NPs exhibit enhanced electrocatalytic EOR activity compared to either monometallic Au or Pd NPs. Specifically, NPs having a 3:1 ratio of Au:Pd exhibit an ~8-fold increase in peak current density compared to Pd NPs, with an onset potential shifted ~200 mV more to the negative compared to Au NPs. Second, the size and composition of AuPd alloy NPs do not (within experimental error) change following 1.0 or 2.0 h chronoamperometry experiments, while monometallic Au NPs increase in size from 2 to 5 nm under the same conditions. Notably, this report demonstrates the importance of post-catalytic ac-STEM/EDS characterization for fully evaluating NP activity and stability, especially for 1-2 nm NPs that may change in size or structure during electrocatalysis.

| S-EPMC9692959 | biostudies-literature