Incorporating fluorine into organic molecules has been shown to have significant benefits to the pharmaceutical industry as fluorine can modify the acidity and lipophilicity of drug candidates, as well as significantly improve the stability and potency of drug molecules. In particular, compounds containing P–F bonds have been shown to be bioactive, acting as inhibitors or as mechanistic probes.  More recently, P–F bonds have a new use in Phosphorus Fluoride Exchange (PFEx), the newest addition to the 2022 Nobel Prize winning click chemistry family. Therefore, it is important to have efficient methods of incorporating P–F bonds into different organic molecules, with deoxyfluorination as the most popular synthetic strategy.  However, deoxyfluorination protocols that generate P–F bonds suffer from severe limitations, such as elevated temperatures (&gt;100 <sup>o</sup>C) and long reaction times (&gt;10 hours). Recently, our laboratory has developed novel sulfone iminium fluoride (SIF) reagents, which are the first reagents capable of performing deoxyfluorination reactions on aliphatic alcohols and carboxylic acids within 60 seconds at room temperature. This work expands the scope of these SIF reagents to the deoxyfluorination of P(V)–OH substrates, presenting the optimization of this new reaction on a model aryl phosphinic acid. The applicability of this protocol is expanded to a variety of other phosphoric substrates, forming a diverse array of P–F bonds.

Expanded use of sulfone iminium fluoride reagents in the rapid deoxyfluorination of phosphoric substrates

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