Direct Synthesis of Amides from Oxidative Coupling of Benzyl Alcohols or Benzylamines with N-Substituted Formamides Using a Cu-Fe-Based Heterogeneous Catalyst

Gupta, S, Nakhate, A, Deshmukh, G, Periasamy, S, Samudrala, S, Bhargava, S and Kantam, M 2018, 'Direct Synthesis of Amides from Oxidative Coupling of Benzyl Alcohols or Benzylamines with N-Substituted Formamides Using a Cu-Fe-Based Heterogeneous Catalyst', ChemistrySelect, vol. 3, no. 29, pp. 8436-8443.


Document type: Journal Article
Collection: Journal Articles

Title Direct Synthesis of Amides from Oxidative Coupling of Benzyl Alcohols or Benzylamines with N-Substituted Formamides Using a Cu-Fe-Based Heterogeneous Catalyst
Author(s) Gupta, S
Nakhate, A
Deshmukh, G
Periasamy, S
Samudrala, S
Bhargava, S
Kantam, M
Year 2018
Journal name ChemistrySelect
Volume number 3
Issue number 29
Start page 8436
End page 8443
Total pages 8
Publisher Wiley - V C H Verlag GmbH & Co. KGaA
Abstract 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 N2 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.
Subject Chemical Sciences not elsewhere classified
Keyword(s) Amidation
Benzyl alcohols
Benzylamines
Cu-Fe metal oxide
DMF
DOI - identifier 10.1002/slct.201801297
Copyright notice © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN 2365-6549
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