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

D. Eilidh Sood, Sue Champion, Daniel M. Dawson, Sonia Chabbra, Bela E. Bode, Andrew C. Sutherland, Allan John Bell Watson

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)
16 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)8460-8463
JournalAngewandte Chemie International Edition
Volume55
Issue number22
Early online date18 Mar 2020
DOIs
Publication statusPublished - 18 May 2020

Keywords

  • Copper
  • Deoxyfluorination
  • Fluorine
  • PET
  • Radiolabeling
  • Alcohols
  • Synthetic methods

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