However, these reactions are still not widely employed in synthetic chemistry laboratories for a variety of reasons, notably a relatively narrow substrate scope and a lack of accessibility (e.g., slow reaction rates; catalysts that are not commercially available or are too expensive). In many cases the reaction scope is quite limited to the preparation of largely unfunctionalized amides. The application of most catalytic reactions to polar substrates and/or those containing coordinating functional groups is often low yielding or unreported. However, these classes of amides are typically the ones most widely in demand for the many applications outlined above. Similarly, catalytic amidation reactions often fail with poorly nucleophilic amines (electron-deficient anilines, heterocyclic amines), and lower yields are frequently obtained from less-reactive carboxylic acids (benzoic acids, heterocyclic carboxylic acids, fluorinated carboxylic acids). This latter factor often correlates with acidity, with carboxylic acids of low pKa typically showing lower reactivity in catalytic amidation processes. Reported catalysts include group(IV) metals, polyoxometallates, silanes/silanols, and boron compounds, with the latter class of catalysts being the most widely studied. Boronic acids have been widely explored as amidation catalysts since the key report using 3,4,5-trifluorophenylboronic acid by Yamamoto in 1996, with catalysts since reported by a number of research groups around the world. Key developments have included bifunctional boronic acid catalysts, and 5-methoxy-2iodophenylboronic acid, the latter an active catalyst at room temperature using molecular sieves as a drying agent. However for coordinating amidation partners (e.g. Aromatic heterocyclic acids + heterocyclic anilines) these catalysts remain ineffective. More recent developments have included diboronic acids and a boron-containing heterocyclic catalyst that is effective with a range of hindered/challenging substrates. Boric acid itself is well-known as a very low-cost catalyst for amidation reactions of relatively reactive substrates, while borate esters have been reported as highly effective catalysts for amidation reactions of a wide-range of substrates, including many acids or amines that were previously considered unsuitable for catalytic amidation reactions (e.g. unprotected amino acids ). We envisaged that by studying the effectiveness of different boronbased amidation catalysts with coordinating substrates we could obtain an understanding of how catalyst deactivation takes place, and which catalysts were more suitable for mediating these challenging catalytic amidation reactions. This in turn should enable the identification of new catalysts that are widely applicable to amidation reactions of coordinating substrates.