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Deoxyfluorination with CuF2: Enabled by Using a Lewis Base Activating Group
Authors:D. Eilidh Sood  Sue Champion  Daniel M. Dawson  Sonia Chabbra  Bela E. Bode  Andrew Sutherland  Allan J. B. Watson
Abstract:Deoxyfluorination is a primary method for the formation of C?F bonds. Bespoke reagents are commonly used because of issues associated with the low reactivity of metal fluorides. Reported here is the development of a simple strategy for deoxyfluorination, using first‐row transition‐metal fluorides, and it 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 in enabling 18F‐radiolabeling is also presented.
Keywords:alcohols  copper  fluorine  radiolabeling  synthetic methods
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