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 |
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Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | 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. |
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ISSN: | 0044-8249 1521-3757 |
DOI: | 10.1002/ange.202001015 |