In preliminary experiments, we studied a simple amidation reaction of 'easy' (i.e. non-functionalised) substrates, 4-phenylbutylamine and benzoic acid in tertiary amyl methyl ether (TAME) under Dean-Stark conditions. A simple boronic acid catalyst (2-chlorophenylboronic acid) led to a considerably faster amidation rate than a reactive borate ester, B(OCH2CF3)3. As we have previously reported, 2chlorophenylborinic acid was catalytically inactive under the same conditions. We have previously observed that 2-aminopyridine is a particularly challenging amine for amidation reactions, perhaps because it is poorly nucleophilic and also contains the adjacent coordinating pyridine nitrogen which is potentially able to chelate to Lewis acids and hence inhibit their ability to mediate amidation. Although B(OCH2CF3)3 has previously worked well for catalytic amidation of a range of challenging substrates, this is often limited to reactions of a challenging amine with a simple carboxylic acid (or vice versa), while reactions of substrate pairs where both partners are deactivated are typically low yielding. We therefore set out to screen a range of borates to identify higher activity catalysts that may be applicable to these more challenging combinations (Figure ).