Organofluorine compounds have seen a significant rise in usage in the pharmaceutical industry due to the various beneficial properties of fluorine such as its potential to increase the lipophilicity, metabolic stability, and binding affinity of an active compound. As a result, fluorination is a highly sought after methodology and the reagents that can quickly and efficiently install fluorine with wide substrate tolerance are of great importance. Sulfone iminium fluorides (SIFs) are a novel class of highly reactive sulfur (VI) molecule capable of achieving deoxyfluorination and sulfur fluoride exchange (SuFEx). These reagents have achieved the deoxyfluorination of alcohols and carboxylic acids in high yields needing just one minute at room temperature to do so.  By far, these are the fastest deoxyfluorination rates to date. SIFs also rapidly engage phenols in SuFEx resulting in the first charged products from the variant on click chemistry methodology. The SIF reagents tolerate a range of functional groups, demonstrated by their usage on medicinally relevant substrates and natural products. The extremely reactive behavior of SIF reagents opens the possibilities of deoxyfluorination of substrates to form heteroatom-fluorine bonds that have seen little previous success such as phosphinic acids, boronic acids, sulfonic acids and silanols.

Enhanced deoxyfluorination and sulfur fluoride exchange  (SuFEx) chemistry via sulfone iminium fluorides

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