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

Sood, D. E., Champion, S., Dawson, D. M., Chabbra, S., Bode, B. E., Sutherland, A. and Watson, A. J. B. (2020) Deoxyfluorination with CuF2: enabled by using a Lewis base activating group. Angewandte Chemie (International Edition), 59(22), pp. 8460-8463. (doi: 10.1002/anie.202001015) (PMID:32109331)

Abstract

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 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 in enabling 18F‐radiolabeling is also presented.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew
• Authors: Sood, D. E., Champion, S., Dawson, D. M., Chabbra, S., Bode, B. E., Sutherland, A., and Watson, A. J. B.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Angewandte Chemie (International Edition)
• Publisher: Wiley
• ISSN: 1433-7851
• ISSN (Online): 1521-3773
• Published Online: 18 March 2020
• Copyright Holders: Copyright © 2020 Wiley-VCH Verlag GMbH and Co. KGaA
• First Published: First published in Angewandte Chemie (International Edition) 59(22): 8460-8463
• Publisher Policy: Reproduced in accordance with the publisher copyright policy