Preparation Of Propargylamines Research Articles

A highly efficient N-rich Cu-MOF heterogeneous catalyst based on N,N-bis(1H-tetrazole- 5-yl)amine for the A3 coupling reaction

The preparation of propargylamines using metal-organic frameworks (MOFs) with high yields in short reaction times is a new method in organic chemistry. A N-rich Cu-MOF catalyst, [Cu(BTA)2]n, with N,N-bis(1(2)H-tetrazol-5-yl)amine (BTA) ligand has been prepared and characterized using FT-IR, XRD, SEM, EDX, and ICP-AES techniques to investigate its performance as a recyclable catalyst in aldehyde-alkyne-amine (A3) coupling reaction for the synthesis of propargylamine derivatives. This catalytic system offers various advantages such as simplicity, high efficiency, short reaction time, and environmental friendliness.

Magnetic nanoparticles modified with a copper(i) complex as a novel and efficient reusable catalyst for A3 coupling leading to C-N bond formation.

Propargylamines are an important and valuable family of nitrogen-containing compounds with many applications in the fields of medical, industrial, and chemical processes. One-pot multicomponent A3 coupling reactions of aldehydes, amines, and alkynes in the presence of transition metals as catalysts is an efficient strategy for preparing propargylamines. In this study, we fabricated a novel magnetically reusable copper nanocatalyst [Fe3O4-BIm-Pyrim-CuI] through the immobilization of the copper(i) complex on the surface of the magnetic nanoparticles modified with benzimidazole-pyrimidine ligand and evaluated its catalytic activity in the preparation of propargylamines through one-pot multicomponent A3 coupling reactions of aldehydes, amines, and alkynes. Under this catalytic system, aryl substrates with both electron-donating and electron-withdrawing substituents also gave the desired products in excellent yields under standardized conditions. The Fe3O4-BIm-Pyrim-CuI catalyst was easily separated using an external magnet, and the recovered catalyst was reused in 8 cycles without significant loss of activity.

Copper Photoredox Catalyzed A3’ Coupling of Arylamines, Terminal Alkynes, and Alcohols through a Hydrogen Atom Transfer Process

AbstractThe first successful example of the three‐component coupling of N‐alkylanilines, terminal alkynes, and alcohols was achieved at room temperature by a visible‐light‐mediated copper‐catalyzed photoredox hydrogen‐atom transfer process. This method allows preparation of propargylamines through uniquely selective α‐C−H bond activation of unactivated alkylalcohols. Preliminary studies indicate that formation of α‐oxy radical is operative. This approach facilitates rapid access to biologically important propargylamines from methanol as an abundant feedstock.

Copper Photoredox Catalyzed A3' Coupling of Arylamines, Terminal Alkynes, and Alcohols through a Hydrogen Atom Transfer Process.

The first successful example of the three-component coupling of N-alkylanilines, terminal alkynes, and alcohols was achieved at room temperature by a visible-light-mediated copper-catalyzed photoredox hydrogen-atom transfer process. This method allows preparation of propargylamines through uniquely selective α-C-H bond activation of unactivated alkylalcohols. Preliminary studies indicate that formation of α-oxy radical is operative. This approach facilitates rapid access to biologically important propargylamines from methanol as an abundant feedstock.

Bis (1(3-trimethoxysilylpropyl)-3-methyl-imidazolium) copper tetrachloride attached to colloidal silica nanoparticles as an efficient catalyst for the preparation of propargylamines

In this research, we reported the successful preparation of bis (1(3-trimethoxysilylpropyl)-3-methyl-imidazolium) copper tetrachloride tethered to colloidal silica nanoparticles and investigated its catalytic application for one-pot multicomponent preparation of propargylamines under microwave irradiation. Ionic liquid tethered to colloidal silica nanoparticles have been characterized by H NMR spectroscopy, scanning electron microscopy, energy dispersive spectroscopy, thermogravimetric analysis, and dynamic light scattering.

Environmentally benign copper nanoparticles supported on walnut shell as a highly durable nanocatalyst for the synthesis of propargylamines

This study was an attempt to prepare copper nanoparticles and to determine their catalytic activity employing walnut shell (WS) residue as a green support and a reusable material. The nanocatalyst was characterized though inductively coupled plasma optical emission spectrometry (ICP-OES), N2-sorption analysis, X-ray powder diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), and transmission electron microscopy (TEM). The catalytic performance of CuNPs@WS was then studied in the preparation of propargylamines via a three-component reaction. The catalyst could be recovered and reused without a significant decrease in its activity over eight reaction cycles. The simple methodology described herein is an economic, ecofriendly and practical method accompanied by higher yields.

Direct addition of alkynes to imines and related CN electrophiles: A convenient access to propargylamines

Propargylic amines are highly useful building blocks in organic synthesis, and the corresponding structural motif has been found in various natural products and compounds of pharmaceutical relevance. This article provides an overview of the most significant advances in the preparation of propargylic amines via the direct addition of alkynes to imines and related carbon-nitrogen electrophiles in the presence of metal catalysts or promoters.

Iridium‐Catalyzed Coupling of Simple Primary or Secondary Amines, Aldehydes and Trimethylsilylacetylene: Preparation of Propargylic Amines.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Enantioselective, Copper(I)‐Catalyzed Three‐Component Reaction for the Preparation of Propargylamines.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Iridium-catalyzed coupling of simple primary or secondary amines, aldehydes and trimethylsilylacetylene: preparation of propargylic amines.

The coupling of amines, aldehydes and trimethylsilylacetylene was found to be promoted in the presence of a catalytic amount of [IrCl(cod)]2; 1 : 1 : 1 or 1 : 2 : 2 coupling products were obtained by allowing primary amine to react with aldehyde and trimethylsilylacetylene.