Fluorine has quickly grown to be a near essential element in drug design, often appearing in multiple places in some of the most prominent and successful pharmaceuticals.  To facilitate this development, chemists have been tasked with devising fluorination protocols that can place this powerful element in various positions on organic molecules.  Deoxyfluorination is one of the most common strategies but, while improvements have been made, limitations still plague this methodology, such as sluggish reaction rates and harsh reagents.  Our laboratory has recently developed a new class of sulfur molecule, sulfone iminium fluorides, that were designed to address many of these limitations.  When used with aliphatic alcohols, sulfone iminium fluorides generate excellent yields of alkyl fluoride products in just 60 seconds, by far the shortest deoxyfluorination reaction times to date.  This enhanced reactivity is not limited to alcohols with acyl fluorides rapidly produced in high yields at room temperature from carboxylic acids.  Moreover, when using phenols, sulfone iminium fluorides participate in Sulfur Fluoride Exchange (SuFEx), one of the more recent additions to the Nobel Prize winning click chemistry family.

Rapid and efficient deoxyfluorination and sulfur fluoride exchange (SuFEx) enabled by sulfone iminium fluorides

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