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Iron/Caffeine as a Catalytic System for Microwave‐Promoted Benzamide Formation
Author(s) -
Bantreil Xavier,
Navals Pauline,
Martinez Jean,
Lamaty Frédéric
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403173
Subject(s) - chemistry , benzamide , catalysis , amide , amine gas treating , caffeine , combinatorial chemistry , organic chemistry , ligand (biochemistry) , microwave , receptor , medicine , biochemistry , physics , quantum mechanics , endocrinology
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 FeCl 2 · 4H 2 O 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.