Deoxyfluorination using CuF2 : enabled by a Lewis base activating group strategy
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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.
Sood , D E , Champion , S , Dawson , D M , Chabbra , S , Bode , B E , Sutherland , A C & Watson , A J B 2020 , ' Deoxyfluorination using CuF 2 : enabled by a Lewis base activating group strategy ' , Angewandte Chemie International Edition , vol. 55 , no. 22 , pp. 8460-8463 . https://doi.org/10.1002/anie.202001015
Angewandte Chemie International Edition
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DescriptionWe thank the University of St Andrews for PhD studentships (D.E.S and S.C.), GlaxoSmithKline and the University of Glasgow for financial support.
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