Deoxyfluorination with CuF 2 : Enabled by Using a Lewis Base Activating Group

Deoxyfluorination with CuF 2 : Enabled by Using a Lewis Base Activating Group

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, a...

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Veröffentlicht in:Angewandte Chemie 2020-05, Vol.132 (22), p.8538-8541
Hauptverfasser: Sood, D. Eilidh, Champion, Sue, Dawson, Daniel M., Chabbra, Sonia, Bode, Bela E., Sutherland, Andrew, Watson, Allan J. B.
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container_issue 22
container_start_page 8538
container_title Angewandte Chemie
container_volume 132
creator Sood, D. Eilidh
Champion, Sue
Dawson, Daniel M.
Chabbra, Sonia
Bode, Bela E.
Sutherland, Andrew
Watson, Allan J. B.
description 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 CuF 2 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 CuF 2 . The utility of the process in enabling 18 F‐radiolabeling is also presented.
doi_str_mv 10.1002/ange.202001015
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