Sulfonimidamides are an emerging class of compounds within medicinal chemistry, and to the best of our knowledge, the synthesis of 2j presents the first application of this moiety within directed C-H activation. Functionalization of acetanilide 2k extends the accessibility of 6-membered iridacyles to oxygen-centered directing groups. Compound 2l was obtained with improved yield by adding cyclopentane carboxylic acid as additive. Improvement of conversion with amide directing groups in combination with carboxylic acid additives was observed during the LSF scope investigation with Bezafibrate 3j (Scheme 2). This observation further extended the scope of accessible directing groups with Weinreb amides, as shown with 2m. This substrate class was unproductive under screening conditions of the directing group informer library (Figure ). While reaction scale-up was vital for further applications, we were also interested in extending the utility of screening libraries by product isolation from small-scale reactions. At 0.02 mmol reaction scale, the products of a series of 10 building blocks were isolated in quantities sufficient for characterization by NMR spectroscopy. The potential utility of small-scale reaction substance isolation extends beyond compound characterization, as a single milligram of compound is often sufficient for in depth biological studies. A common set-back of this approach are reduced product yields due to sample handling and purification-associated loses, as demonstrated with the decreased yields of 2d and of 2e (Scheme 1, top vs. bottom). The applicability of heterocyclic DGs was further demonstrated with dihydrooxazole 1n, thiazole 1o, benzothiazole 1p, pyrimidine 1q and pyridazine 1r. The PMP-capped imine 2s was obtained with low yield as a result of hydrolysis during purification. Products from oxygen-centered directing groups in N-acetyl indoline 2t and N-methyl benzamide 2u were also isolated, the latter with lower yield due to problematic separation from unreacted starting material.