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Deoxyfluorination Using CuF2

preprint
submitted on 06.12.2019 and posted on 13.12.2019 by D. Eilidh Sood, Sue Champion, Daniel M. Dawson, sonia chabbra, Bela E. Bode, Andrew Sutherland, Allan Watson
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.

Funding

University of St Andrews

GlaxoSmithKline

History

Email Address of Submitting Author

aw260@st-andrews.ac.uk

Institution

University of St Andrews

Country

United Kingdom

ORCID For Submitting Author

0000-0002-1582-4286

Declaration of Conflict of Interest

The authors declare no conflicts of interest.

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