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
Copyright © 2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/anie.202001015
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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