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Iron/Caffeine as a Catalytic System for Microwave-Promoted Benzamide Formation

Authors :
Bantreil, Xavier
Navals, Pauline
Martinez, Jean
Lamaty, Frédéric
Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM)
Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)
Source :
European Journal of Organic Chemistry, European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (2), pp.417-422. ⟨10.1002/ejoc.201403173⟩
Publication Year :
2015
Publisher :
HAL CCSD, 2015.

Abstract

International audience; The amide bond is an essential unit in many drugs and polymers. The catalyzed oxidation of alcohols and amines is an effective method to form amides with limited undesired waste. Herein, we demonstrate the beneficial effect of microwave activation for this reaction. The benzamides were directly formed from alcohols and amine hydrochloride salts in short reaction times with yields up to 84 % and TOFs (turnover frequencies) up to 33.6 h–1. Among the examined transition metals, only nontoxic and inexpensive FeCl2·4H2O together with caffeine as a stabilizing ligand provided a uniquely efficient catalytic system for the transformation. Natural sources of caffeine were also evaluated under the amidation conditions.

Details

Language :
English
ISSN :
1434193X and 10990690
Database :
OpenAIRE
Journal :
European Journal of Organic Chemistry, European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (2), pp.417-422. ⟨10.1002/ejoc.201403173⟩
Accession number :
edsair.dedup.wf.001..e4c727223532ae20c38e483ab7ae674b
Full Text :
https://doi.org/10.1002/ejoc.201403173⟩