Boric Acid Catalyzed Direct Amidation between Amino-Azaarenes and Carboxylic Acids

^‡ These authors contributed equally to this work.

Abstract

A novel and facile boric acid catalyzed direct amidation between amino-azaarene compounds and carboxylic acids has been developed. The amidation proceeded cleanly and provided good to excellent yields of the desired amides. Boric acid is a green and inexpensive catalyst. We have also found that N,N,N′,N′-tetramethylpropane-1,3-diamine acted as an additive accelerating this boric acid catalyzed amidation. A mixed acid anhydride is postulated to be the active intermediate responsible for this successful amidation. This direct amidation is an atom- and step-economical reaction.

Key words

amidation - boric acid - azaarenes - aminopyridine - N,N,N′,N′-tetramethylpropane-1,3-diamine

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