Synthesis Of Propargylamines Research Articles

Modified Montmorillonite Clay Stabilized Silver Nanoparticles: An Active Heterogeneous Catalytic System for the Synthesis of Propargylamines

We have synthesized size selective silver nanoparticles (Ag-NPs) in the nanopores of modified montmorillonite clay by an “in situ” approach. The modification of montmorillonite K-10 was carried out with HCl under controlled condition for generating a high surface area and porous matrix which acted as hosts for the “in situ” generation of silver nanoparticles. The synthesized nanocomposite material was well characterized by UV–Visible spectroscopy, powder XRD, N2 adsorption–desorption isotherm and TEM analysis. UV–Visible and TEM study revealed silver nanoparticles of 0–10 nm were evenly distributed on the support. The Ag-NPs stabilized on modified montmorillonite serves as an efficient green heterogeneous catalyst for the three component one-pot synthesis of propargylamines with 83–95 % yield and 100 % selectivity under mild reaction condition. The nanocatalyst can be recycled several times without any significant loss in its catalytic activity. Ag-NPs@mmt is found to be an efficient and robust heterogeneous catalyst for the synthesis of propargylamines under mild reaction condition.

Zn(ii) anchored onto the magnetic natural hydroxyapatite (ZnII/HAP/Fe3O4): as a novel, green and recyclable catalyst for A3-coupling reaction towards propargylamine synthesis under solvent-free conditions

In this paper, Zn(ii) anchored onto the magnetic natural hydroxyapatite (ZnII/HAP/Fe3O4), as a new and magnetically recoverable catalyst, was prepared and characterized using different techniques such as FT-IR, XRD, TGA, TEM, EDX, VSM and ICP.

Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)2

Copper-Catalyzed Coupling of Alkynes and Amines for the Synthesis of Propargyl Amines in the Presence of PhI(OAc)₂

Highly Efficient and Green Synthesis of Propargylic Amines Catalyzed by Waste Crab Shell Powders-Supported CuI Catalyst

A series of propargylic amines were synthesized from terminal alkynes, dichloromethane and organic amines by using waste crab shell powders supported-CuI (CSPs-CuI) as catalyst. Using waste crab shell powders as catalyst support, not only resolve the problem of environment pollution and resources waste, but also produce propargylic amines through a highly efficient and green method. CSPs-CuI was characterized by Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TG) and atomic absorption spectroscopy (AAS). The reaction conditions were optimized by the investigation of catalyst support and base types. The propargyllic amines were obtained readily in intermediate to excel- lent yields under the optimal reaction condition. CSPs-CuI showed good reusability and could be recovered easily through filtration and washing. It was reused at least 4 times without obvious loss of catalytic performance.

Copper nanoparticles supported on starch micro particles as a degradable heterogeneous catalyst for three-component coupling synthesis of propargylamines

Starch supported Cu NPs as a degradable heterogeneous catalyst for A3 coupling reaction.

Synthesis and characterization of a Cu(ii) Schiff base complex immobilized on graphene oxide and its catalytic application in the green synthesis of propargylamines

A Cu(ii) Schiff base complex immobilized on graphene oxide has been synthesized and characterized by FTIR, FT-RAMAN, XRD, UV, TEM, FE-SEM, EDAX, TGA, N2 adsorption–desorption and AAS analysis.

Gold Nanoparticles Supported on Polyacrylamide Containing a Phosphorus Ligand as an Efficient Heterogeneous Catalyst for Three-Component Synthesis of Propargylamines in Water

Gold nanoparticles supported on a polyacrylamide containing a phosphinite ligand have been synthesized and characterized using different techniques such as TEM, SEM, EDX, XPS, and solid UV analyses. The new material was successfully applied as a heterogeneous catalyst for the three-component A3 coupling of amines, aldehydes, and alkynes to give propargylamines. Reactions are performed in neat water at 80 °C with only 0.05 mol% catalyst loading. The heterogeneous catalyst is recyclable during seven consecutive runs with small decrease in activity.

ChemInform Abstract: Continuous Flow Reactions in Water for the Synthesis of Propargylamines via a Metal‐Free Decarboxylative Coupling Reaction.

AbstractAlkynyl carboxylic acids undergo decarboxylative coupling with amines and paraformaldehyde, using a continuous flow reaction system to give propargylamines in excellent yields.

Efficient Rhodium-Catalyzed Multicomponent Reaction for the Synthesis of Novel Propargylamines.

[{Rh(μ-Cl)(H)2 (IPr)}2 ] (IPr = 1,3-bis-(2,6-diisopropylphenyl)imidazole-2-ylidene) was found to be an efficient catalyst for the synthesis of novel propargylamines by a one-pot three-component reaction between primary arylamines, aliphatic aldehydes, and triisopropylsilylacetylene. This methodology offers an efficient synthetic pathway for the preparation of secondary propargylamines derived from aliphatic aldehydes. The reactivity of [{Rh(μ-Cl)(H)2 (IPr)}2 ] with amines and aldehydes was studied, leading to the identification of complexes [RhCl(CO)IPr(MesNH2 )] (MesNH2 = 2,4,6-trimethylaniline) and [RhCl(CO)2 IPr]. The latter shows a very low catalytic activity while the former brought about reaction rates similar to those obtained with [{Rh(μ-Cl)(H)2 (IPr)}2 ]. Besides, complex [RhCl(CO)IPr(MesNH2 )] reacts with an excess of amine and aldehyde to give [RhCl(CO)IPr{MesNCHCH2 CH(CH3 )2 }], which was postulated as the active species. A mechanism that clarifies the scarcely studied catalytic cycle of A3 -coupling reactions is proposed based on reactivity studies and DFT calculations.

Asymmetric synthesis of syn-propargylamines and unsaturated β-amino acids under Brønsted base catalysis.

Propargylamines are important intermediates for the synthesis of polyfunctional amino derivatives and natural products and biologically active compounds. The classic method of synthesizing chiral propargylamines involves the asymmetric alkynylation of imines. Here, we report a significant advance in the catalytic asymmetric Mannich-type synthesis of propargylamines through catalytic asymmetric addition of carbon nucleophiles to C-alkynyl imines, culminating in a highly syn-selective catalytic asymmetric Mannich reaction of C-alkynyl imines that provide syn-configured propargylamines with two adjacent stereogenic centres and a transition metal-free organocatalytic asymmetric approach to β-alkynyl-β-amino acids with high efficiency and practicality, via a chiral Brønsted base-catalysed asymmetric Mannich-type reaction of in situ generated challenging N-Boc C-alkynyl imines from previously unreported C-alkynyl N-Boc-N,O-acetals, with α-substituted β-keto esters and less-acidic malonate (thio)esters as nucleophiles, respectively. A catalytic activation strategy is also disclosed, which may have broad implications for use in catalysis and synthesis.

ChemInform Abstract: Aldehyde—Alkyne—Amine (A3) Coupling Catalyzed by a Highly Efficient Dicopper Complex.

AbstractThe dicopper(I) complex shown is found to be a highly efficient catalyst for the synthesis of various propargyl amines via multicomponent reaction of aldehydes, alkynes, and secondary amines under mild reaction conditions.

ChemInform Abstract: Facile and Diverse Microwave‐Assisted Synthesis of Secondary Propargylamines in Water Using CuCl/CuCl2.

AbstractThe novel protocol provides a wide range of secondary propargylamines equipped with diverse substituents in generally high yields.

Continuous flow reactions in water for the synthesis of propargylamines via a metal-free decarboxylative coupling reaction

A range of propargylamines was synthesized via the metal-free decarboxylative coupling of alkynyl carboxylic acids with amines and paraformaldehyde in water, using a continuous flow reaction system. Aryl- and alkyl-substituted propiolic acids were found to react with secondary amines in the presence of paraformaldehyde, at 140°C in water to give the desired propargylamines in good yield.

ChemInform Abstract: Metal‐Free Multicomponent Coupling Reaction of Aliphatic Amines, Formaldehyde, Organoboronic Acids, and Propiolic Acids for the Synthesis of Diverse Propargylamines.

Abstract A metal-free multicomponent coupling reaction of aliphatic amines, formaldehyde, organoboronic acids, and propiolic acids has been reported for the synthesis of diverse propargylamines. This transformation involves a MCR2 of PBM and decarboxylative three-component coupling reactions.

Magnetic CuO nanoparticles supported on graphene oxide as an efficient catalyst for A3-coupling synthesis of propargylamines

Abstract Magnetically separable CuO nanoparticles supported on graphene oxide (Fe 3 O 4 NPs/GO–CuO NPs) is synthesized and characterized for the preparation of propargylamines in EtOH, at 90 °C. Fe 3 O 4 NPs/GO–CuO NPs is found to be an efficient catalyst for the A 3 -coupling of aldehydes, amines, and alkynes through C H activation. Both aromatic and aliphatic aldehydes and alkynes are combined with secondary amines to provide a wide range of propargylamines in moderate to excellent yields.

ChemInform Abstract: A Sulfonate‐Based Cu(I) Metal‐Organic Framework as a Highly Efficient and Reusable Catalyst for the Synthesis of Propargylamines under Solvent‐Free Conditions.

Abstractvia three‐component reaction of cyclic amines, aromatic aldehydes and alkynes

Development of gold nanoparticle-fungal hybrid based heterogeneous interface for catalytic applications

Unsupported and free gold nanoparticles (Au NPs) represent great potential in the field of catalysis. However, shortcomings like agglomeration and loss of the precious catalyst has encouraged the development of supported Au NPs as catalyst with increased activity, selectivity, ease of separation from the reaction mixture and recyclability. The present work demonstrates an eco-friendly, rapid and facile synthesis of catalytically active bio-supported Au NPs using a soil fungus, Aspergillus japonicus AJP01. The dual role of the fungal isolate in synthesis as well as immobilization of Au NPs is the remarkable feature of the study. The fungus successfully reduced Au(III) into Au NPs containing principally Au(0) with a small percentage of Au(I) as revealed by X-ray photoelectron spectroscopy. The particles were spherical in shape and well distributed on fungal mycelia with size ranging predominantly between 15 and 20nm. The as-synthesized nanoparticle-fungal hybrid was found to be highly efficient in catalyzing sodium borohydride mediated reduction reactions of 4-nitrophenol and hexacyanoferrate(III). The versatility of the bionanocatalyst was further demonstrated by catalyzing the A3 coupling reactions for the synthesis of propargylamines.

ChemInform Abstract: Mild and Catalyst‐Free Petasis/Decarboxylative Domino Reaction: Chemoselective Synthesis of N‐Benzyl Propargylamines.

Multicomponent domino reactions are attractive for assembling functionalized compounds. To this end, a one-pot catalyst-free chemoselective synthesis of N-benzyl propargylamines is reported with good functional group compatibility. This mild process involves in situ formation of an active amine through Petasis reaction of primary amines, formaldehyde solution, and boronic acids, which reacts with propiolic acids to give product in up to 94% yield via decarboxylative coupling reaction.

Euphorbia helioscopia Linn as a green source for synthesis of silver nanoparticles and their optical and catalytic properties

During this study, we report the green synthesis of silver nanoparticles (Ag NPs) using Euphorbia helioscopia Linn leaf extract for the synthesis of propargylamines. Also, the structural and optical properties are studied. The synthesized nanoparticles are characterized by TEM, XRD, FT-IR and UV–visible techniques. UV–visible studies show an absorption band at 440nm due to surface plasmon resonance (SPR) of the silver nanoparticles. Furthermore, the catalyst exhibits high catalytic activity, superior cycling stability and excellent substrate applicability.

Cu2O/nano-CuFe2O4: A novel and recyclable magnetic catalyst for three-component coupling of carbonyl compounds–alkynes–amines under solvent-free condition

Cu2O/nano-CuFe2O4 magnetic composite with different loadings of Cu2O has been synthesized by feasible and low-cost method. The as-prepared composite was fully characterized by FT-IR, XRD, FEG-SEM, EDS and VSM analyzer. The catalytic activity of magnetic composite for synthesis of propargylamines was evaluated. The catalyst has many obvious advantages and easily separated via an external magnet. It can be reused for five successive runs.