Synthesis of a Novel Magnetic Reusable Organocatalyst Based on 4‐Dialkylaminopyridines for Acyl Transformations

Abstract

In this study, we have developed the synthesis of a new magnetic nanoparticles‐supported 4‐(dimethylamino)pyridine (DMAP)‐based catalyst to be use as a robust heterogeneous organocatalyst in organic transformations. The MNP‐DMAP is readily synthesized by a simple synthetic route from cheap and commercially accessible starting materials using normal laboratory techniques. To synthesize of MNP‐DMAP catalyst, silica‐coated magnetic nanoparticles (Fe3O4@SiO2) were reacted with trimethoxy(vinyl)silane to produce vinyl‐functionalized magnetic nanoparticles (VMNP). Subsequently, VMNP was oxidized to generate the MNP–oxiran (MNPO) material. Reaction of a MNPO substrate with N‐methylpyridin‐4‐amine resulted in the production of MNP‐DMAP catalyst. The MNP‐DMAP material was characterized using different techniques such as FT‐IR, XRD, TEM, SEM, EDX, VSM, TGA, and elemental analysis. The catalytic activity of MNP‐DMAP was evaluated in the acylation of hydroxyl and amino functionalized substrates under mild and solvent‐free conditions. The catalyst was very efficient in the reactions and it was reusable at least for 16 times without significant decreasing in its catalytic activity.

Supported Palladium on Magnetic Nanoparticles–Starch Substrate (Pd-MNPSS): Highly Efficient Magnetic Reusable Catalyst for C–C Coupling Reactions in Water

“…According to the FT-IR spectrum of Fe 3 O 4 @SiO 2 , the absorption peaks observed at 590 cm –1 are associated with the vibration of the Fe–O bond . The broad band depicted at 3408 cm –1 is attributed to the stretching vibration of O–H . Two peaks observed at 1131 and 976 cm –1 are assigned to the symmetrical and asymmetrical vibrations of the Si–O–Si bonds, confirming the silica-coated layer on the MNP surface…”

“…46 The broad band depicted at 3408 cm −1 is attributed to the stretching vibration of O−H. 47 Two peaks observed at 1131 and 976 cm −1 are assigned to the symmetrical and asymmetrical vibrations of the Si−O−Si bonds, confirming the silica-coated layer on the MNP surface. 48 The presence of the vibration band at 594 cm −1 refers to the Si−Cl bond in the structure of Fe 3 O 4 @SiO 2 @Cl material.…”

Heterogeneous SO3H@Fe3O4 magnetic nanocatalyst as an efficient and reusable medium for the synthesis of 3,3′‐(arylmethylene)‐bis‐(4‐hydroxycoumarin), bis‐(indolyl)‐methane, and 1,8‐dioxo‐octahydroxanthene derivatives

“…[10,11] Iron oxide magnetic nanoparticles (MNPs) for the immobilization of the organic groups onto a surface with a strong connection are most interesting because of their easy synthesis and functionalization, high surface area, good stability, and low toxicity and price. [12][13][14] Because of their strong magnetic moments, these nanoparticles show different types of potential applications in drug delivery, cell sorting, hyperthermal agents, and Magnetic resonance imaging contrast agents. [15][16][17][18][19][20] Heterocyclic compounds, also called heterocycles, are extremely spread across nature and are essential for living organisms.…”

Oxime palladacycle in PEG as a highly efficient and recyclable catalytic system for phenoxycarbonylation of aryl iodides with phenols

“…Several attempts have been made for the synthesis aromatic esters by a non‐classical carbonylative approach such as the (i) reaction between carboxylic acid with phenol or alcohol using “lewis” acid or another strong acid such as hydrochloric acid, sulphuric acid (ii) acylation of alcohol/phenol with an acyl chloride or acid anhydride (iii) alkylation of carboxylate salts of alkali/alkaline earth metal, silver and copper . Alternatively, palladium catalyzed carbonylation of aryl halide has been emerging most potent and convenient methodology for the synthesis of carboxylic derivative pioneered by Heck in 1970 .…”