Deoxofluor

DeoxoFluor is a chemical reagent used in organic synthesis for deoxyfluorination, the conversion of alcohols to alkyl fluorides. It is part of a family of reagents including DAST and XtalFluor that enable replacement of hydroxyl groups with fluorine under relatively mild conditions. DeoxoFluor is marketed as a safer and more stable alternative to DAST, offering broad substrate scope and compatibility with many functional groups.

In typical applications, primary and secondary alcohols are treated with DeoxoFluor in an inert, dry solvent (such as dichloromethane) at 0–25 °C, often in the presence of a base or additive to scavenge byproducts. The reaction proceeds via activation of the hydroxyl group to a good leaving group, followed by fluoride attack to furnish the alkyl fluoride and sulfur-containing byproducts.

The reagent is widely used in pharmaceutical and medicinal chemistry for the synthesis of fluorinated intermediates, enabling late-stage fluorination and the introduction of fluorine that can affect metabolic stability, lipophilicity, and bioavailability. It is compatible with many functional groups but remains moisture-sensitive and potentially hazardous; it should be handled under strictly controlled conditions with appropriate personal protective equipment, in a fume hood, and stored refrigerated to minimize decomposition.

Related topics include other deoxyfluorination reagents such as DAST and XtalFluor reagents.