A Novel Recyclable Ni/Cu/Fe Termetallic Nanocatalyst for the Synthesis of Propargylamines through the A³‐Coupling Reactions

Abstract

A novel Ni/Cu/Fe nanocatalyst was prepared via a three‐step procedure for the A3‐coupling reaction of an aldehyde, an amine, and a terminal alkyne to synthesize the corresponding propargylamine. Oleic acid was used in the second step to avoid aggregation of CuFe2O4 nanoparticles. The prepared NiO/OA‐CuFe2O4 (Ni/Cu/Fe) was characterized using X‐ray diffraction (XRD), scanning electron microscopy/wavelength dispersive X‐ray (SEM/WDX), particle size analyzer, fourier transform infrared (FT‐IR) and atomic absorption spectroscopy (AAS). A variety of propargylamines was synthesized using a very small amount of this efficient and inexpensive nanocatalyst in toluene as the solvent at 100 °C. Due to high magnetic properties of the prepared catalyst, its isolation and recycle were very easy, and it was used in five repetitive cycles.

Synthesis, characterization, and reactivity of a novel magnetically recyclable triazine‐based Cu–NNN–pincer complex

“…Due to the importance of propargylamines, various metal complexes and salts have been used to achieve this reaction under homogeneous or heterogeneous conditions. [20,27,[62][63][64][65][66][67][68] In continuation of our previous research on the development of functionalized nanocatalysts and their applications in various organic transformations, [69][70][71] herein, we report a novel heterogeneous and recyclable triazine-based Cu-NNN-pincer complex, Fe 3 O 4 @SiO 2 -NH-CCl-AT-Cu(II), as a novel, nontoxic, and low-cost catalyst for the preparation of propargylamines from A 3 coupling reactions of aldehydes, phenylacetylene, and amines.…”

“…Due to the importance of propargylamines, various metal complexes and salts have been used to achieve this reaction under homogeneous or heterogeneous conditions. [ 20,27,62–68 ]…”

TMU‐16‐NH2MOF modified with organic ligands for stabilization of copper nanoparticles: An efficient and crystalline heterogeneous catalyst for the synthesis of propargyl amines derivatives under green reaction condition

“…[2] Unfortunately, these materials must be applied in stoichiometric amounts, as well as usually moisture sensitive, and thus required strictly to control reaction conditions. [3] Using transition-metal catalysts in the three-component coupling of aldehydes or ketones, amines, and alkynes named A 3 -coupling is a simple and straightforward method to synthesize propargylamines via the C H activation reaction. In this reaction, water is the sole theoretical byproduct and is often catalyzed by homogeneous catalytic systems.…”

One‐pot Synthesis of Propargylamines using Aldehydes‐Amines‐Acetylene via an Efficient Nickel‐Based Silica‐Coated Magnetic Nanocatalyst

“…coupled aldehydes, secondary amines and phenylacetylene using Cu−Ni bimetallic reusable catalyst [9] . Another Ni/Cu/Fe termetallic catalyst has also been utilized for the synthesis of propargylamines [10] . However, most of these methods are associated with various drawbacks such as high cost, use of bimetallic and trimetallic catalysts and difficulty in separation from reaction mixture.…”