Deoxyfluorination using CuF2 : enabled by a Lewis base activating group strategy
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.
Citation
Sood , D E , Champion , S , Dawson , D M , Chabbra , S , Bode , B E , Sutherland , A C & Watson , A J B 2020 , ' Deoxyfluorination using CuF 2 : enabled by a Lewis base activating group strategy ' , Angewandte Chemie International Edition , vol. 55 , no. 22 , pp. 8460-8463 . https://doi.org/10.1002/anie.202001015
Publication
Angewandte Chemie International Edition
Status
Peer reviewed
ISSN
1433-7851Type
Journal article
Description
We thank the University of St Andrews for PhD studentships (D.E.S and S.C.), GlaxoSmithKline and the University of Glasgow for financial support.Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.