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

Xavier Bantreil (1) , Pauline Navals (1) , Jean Martinez (1) , Frédéric Lamaty (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

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.

Mots clés: Iron; Amides; Microwave chemistry; Homogeneous catalysis; Oxidation

Domaines: Chimie organique; Catalyse

Xavier Bantreil, Pauline Navals, Jean Martinez, Frédéric Lamaty. Iron/Caffeine as a Catalytic System for Microwave-Promoted Benzamide Formation. European Journal of Organic Chemistry, 2015, 2015 (2), pp.417-422. ⟨10.1002/ejoc.201403173⟩. ⟨hal-01114591⟩