Mechanism + Description
PhenoFluor serves to activate the alcohol/phenol forming a alkoxy-/phenoxy-imidazolium bifluoride salt, which can be displaced in an SN2 fashion by fluoride.
PhenoFluor is a unique reagent in being able to mediate the deoxyfluorination of both alcohols and phenols depending on the conditions employed. It has been utilized for the late stage deoxyfluorination of a series of complex bioactive substances with good functional group tolerance, and predictable reactivity for poly-hydroxylated system. It's use on scale may be limited due to lack of bulk commercial availability. In addition, the reagent is poor from an atom economy standpoint, and displays a degree of moisture sensitivity, though the latter issue has been mitigated by the development of alternative formulations.
Relevant scale up examples