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Naji, M. |
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Motta, Antonella |
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Aletan, Dirar |
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Mohamed, Tarek |
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Ertürk, Emre |
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Taccardi, Nicola |
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Petrov, R. H. | Madrid |
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Alshaaer, Mazen | Brussels |
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Bih, L. |
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Casati, R. |
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Kočí, Jan | Prague |
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Azam, Siraj |
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Ospanova, Alyiya |
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Blanpain, Bart |
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Ali, M. A. |
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Popa, V. |
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Rančić, M. |
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Ollier, Nadège |
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Azevedo, Nuno Monteiro |
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Landes, Michael |
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Rignanese, Gian-Marco |
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Bhargava, Suresh K.
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article
Direct Synthesis of Amides from Oxidative Coupling of Benzyl Alcohols or Benzylamines with N-Substituted Formamides Using a Cu-Fe-Based Heterogeneous Catalyst
Abstract
<p>Here we report a highly active and recyclable Cu−Fe based heterogeneous catalytic system for the oxidative coupling of benzyl alcohols as well as benzylamines with N-substituted formamides. The Cu−Fe Metal Oxide (Cu−Fe MO) catalyst was prepared by a co-precipitation method and was characterized by X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Energy-dispersive X-ray spectroscopy (EDS), Field Emission Gun-Scanning Electron Microscopy (FEG-SEM) and N<sub>2</sub> physical adsorption techniques. The catalytic activity of the as-prepared Cu−Fe MO catalyst was evaluated towards amidation reactions and a broad spectrum of aromatic amides have been synthesized in good to moderate yields by oxidative coupling of benzyl alcohols or benzylamines bearing various substituents with N-substituted formamides. The control experiments revealed that the benzyl alcohol or benzylamine gets converted to an acyl radical and on the other side the N-substituted formamides form an aminyl radical in presence of the catalyst and tert-Butyl hydroperoxide (TBHP). Successive coupling of the in-situ generated acyl and aminyl radicals affords the desired product amide. Furthermore, the heterogeneous Cu−Fe MO catalyst recycled for four times towards the amidation of benzyl alcohol and the fidelity of the spent catalyst has been confirmed by XRD analysis.</p>