Fluorine is one of the more privileged atoms of the periodic table and has been frequently used in the pharmaceutical industry to increase metabolic stability and lipophilicity of potential drug targets. Because of this, a great deal of attention has been given to developing different approaches to incorporate fluorine into organic molecules. One key method for installing fluorine into organic molecules is deoxyfluorination, a process that replaces an oxygen-containing functional group with fluorine. Our lab has recently developed novel sulfone iminium fluoride (SIF) reagents that reacts with alcohols and carboxylic acids in under 60 seconds with high efficiency. Our current goal is to compare the reactivity of these new SIF reagents with known sulfonimidoyl fluoride reagents to establish a trend in reactivity. In particular, we will focus on converting benzoic acid substrates into acyl fluorides utilizing various conditions to reach optimal reactivity and yield.

Comparison of sulfonimidoyl fluorides to novel sulfone iminium fluorides in the deoxyfluorination of carboxylic acids

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