An Fe3O4@SiO2/Schiff base/Pd complex as an efficient, heterogeneous magnetically recoverable and reusable catalyst for the N-arylation of O-alkyl primary carbamates.
A palladium‐catalyzed domino method for the direct synthesis of carbamates and ureas has been developed by using readily available and economical starting materials (aryl halide, carbon monoxide, sodium azide, amines and alcohols) in a one‐pot approach. The domino process underwent carbonylation, Curtius rearrangement, and nucleophilic addition. This protocol provides a step‐economical and highly efficient reaction to access the wide range of valuable carbamates, symmetrical and unsymmetrical ureas with high yields under remarkable mild reaction conditions that are important factors in pharmaceutical science, biochemistry and agricultural industries. Furthermore, the magnetically recoverable nanocatalyst (Fe3O4@SiO2/Pd(II)) can be conveniently and swiftly recycled using external magnet and reused at least for seven times without noticeable loss of its catalytic activity.
The synthesis of inexpensive and novel air-stable Ni(0) nanoparticles immobilized on the EDTA-modified Fe 3 O 4 @SiO 2 nanocatalyst was investigated in Suzuki-Miyaura and Heck cross-coupling reactions. This catalytic system displayed a greatly improved substrate scope for the carbon-carbon bond formations starting from a wide range of green and economical electrophiles aryl and heteroaryl carbamates and sulfamates via highly efficient method under mild, operationally simple reaction conditions. The synthesized heterogeneous catalyst was also fully characterized by FT-IR, TEM, XRD, DLS, FE-SEM, UV-Vis, EDX, XPS, TGA, NMR, VSM, ICP and elemental analysis techniques. The heterogeneous magnetic nanocatalyst can easily be recovered by an external magnetic field and reused for the next reactions for at least seven times with negligible leaching of catalyst and no substantial decrement in the activity. All these highlights have made the present protocol an interesting, simple and environmentally benign process with low catalyst loading and easy manipulations.
A convenient and efficient selective mono N-arylation of primary O-alkyl thiocarbamates and carbamates is reported by a recyclable magnetic Cu(ii) nanocatalyst.
Superparamagnetic Fe3O4 nanoparticles were used to synthesize various primary carbamates as well as monosubstituted and N,N‐disubstituted ureas. This efficient phosgene‐free process used urea as an eco‐friendly carbonyl source in the presence of a biocompatible deep eutectic solvent (DES) to provide an inexpensive and attractive route that afforded the products in moderate to excellent yields. The employed DES serves both a catalytic role and as the green reaction medium. The magnetic nanocatalyst and DES can been reused several times without a significant loss of activity.
A highly
efficient and air-, thermal-, and moisture-stable nickel-based
catalyst with excellent magnetic properties supported on silica-coated
magnetic Fe3O4 nanoparticles was successfully
synthesized. It was well characterized by Fourier transform infrared
spectroscopy, powder X-ray diffraction, transmission electron microscopy,
field emission scanning electron microscopy, thermogravimetric analysis,
dynamic light scattering (DLS), X-ray photoelectron spectroscopy,
vibration sample magnetometry, energy-dispersive X-ray analysis, inductively
coupled plasma analysis, and nitrogen adsorption–desorption
isotherm analysis. The Suzuki–Miyaura coupling reaction between
aryl carbamates and/or sulfamates with arylboronic acids was selected
to demonstrate the catalytic activity and efficiency of the as-prepared
magnetic nanocatalyst. Using the mentioned heterogeneous nanocatalyst
in such reactions generated corresponding products in good to excellent
yields in which the catalyst could easily be recovered from the reaction
mixture with an external magnetic field to reuse directly for the
next several cycles without significant loss of its activity.
A simple and efficient solvent-free preparation of primary carbamates, S-thiocarbamates and ureas from alcohols, phenols, thiols and amines in the presence of 4-dodecylbenzenesulfonic acid, as a cheap and green Brønsted acid, has been described.
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