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Deoxyfluorination Using CuF2

preprint
submitted on 06.12.2019, 16:26 and posted on 13.12.2019, 11:18 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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