Deoxyfluorination using CuF2 : enabled by a Lewis base activating group strategy

Abstract

Deoxyfluorination is a primary method for the formation of C–F bonds. Bespoke reagents are commonly used due to issues associated with the low reactivity of metal fluorides. Here, we report the development of a simple strategy for deoxyfluorination using first‐row transition metal fluorides that overcomes these limitations. Using CuF2 as an exemplar, activation of an O ‐alkylisourea adduct formed in situ allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2 . The utility of the process towards enabling 18F‐radiolabeling is also presented.