Copper–birhodanine complex immobilized on Fe₃O₄ nanoparticles: DFT studies and heterogeneous catalytic applications in the synthesis of propargylamines in aqueous medium

Abstract

Heterogeneous magnetic nanocatalyst, Fe3O4@SiO2–Ligand–Cu (II) MNPs, reveals high catalytic performance within the synthesis of propargylamines using the multicomponent coupling reaction of aldehydes, phenylacetylene and secondary amines in water as a solvent. The substantial feature of this organic–inorganic hybrid magnetic nanocatalyst is the capability of straightforward separation of the reaction mixture by an external magnet which was retrieved ten times without significant loss of catalytic activity. This methodology has other advantages such as subordination to the principles of green chemistry and avoiding the use of expensive and harmful organic solvents. To study the stability and actual structure of birhodanine derivative–copper (II) complex, DFT calculations were also performed.

Boehmite@SiO2@ Tris (hydroxymethyl)aminomethane‐Cu(I): a novel, highly efficient and reusable nanocatalyst for the C‐C bond formation and the synthesis of 5‐substituted 1H‐tetrazoles in green media

“…[40] However, the homogenous Cu complexes suffer from significant drawbacks; including, the difficulty of separation and recovery of Cu complexes from the reaction system, high costs and the potential environmental pollution. [41][42][43] However, separation, purification, and reusability of homogeneous catalysts are tedious process. [44][45][46][47] On the other hand, easy separation and consecutive reusability of heterogeneous catalyst makes their consideration for industrial and laboratorial aims.…”

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

“…In continuation of our previous research on the development of functionalized nanocatalysts and their applications in various organic transformations, [ 69–71 ] 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.…”

“…The synthetic methods of these MNPs, with some modifications, have been reported in our prior articles (Supporting Information S1, ESI 2–4). [ 69–71 ]…”

Preparation, characterization and heterogeneous catalytic applications of GO/Fe3O4/HPW nanocomposite in chemoselective and green oxidation of alcohols with aqueous H2O2

“…Therefore, with regard to the cases cited above and in the continuation of our activities in the synthesis of nanoparticles and nanocomposites and their applications in organic synthesis, we planned to design and synthesize GO/Fe 3 O 4 /HPW nanocomposite as a catalytic system with the hope that this system has unique catalytic properties of heteropoly acids and high surface area to have a heterogeneous condition which allows high stability and easy separation from the reaction mixture (Scheme ). In continuation, we employed a facile and efficient approach for chemoselective oxidation of alcohols to corresponding aldehydes or ketones catalyzed by GO/Fe 3 O 4 /HPW nanocomposite with H 2 O 2 under organic solvent ‐ free conditions.…”