Sood D Eilidh, Champion Sue, Dawson Daniel M, Chabbra Sonia, Bode Bela E, Sutherland Andrew, Watson Allan J B
EaStCHEM, School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK.
West of Scotland PET Centre, Greater Glasgow and Clyde NHS Trust, Glasgow, G12 OYN, UK.
Angew Chem Int Ed Engl. 2020 May 25;59(22):8460-8463. doi: 10.1002/anie.202001015. Epub 2020 Mar 18.
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 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 . The utility of the process in enabling F-radiolabeling is also presented.
脱氧氟化是形成碳-氟键的主要方法。由于金属氟化物反应活性低的问题，通常使用定制试剂。本文报道了一种使用第一行过渡金属氟化物进行脱氧氟化的简单策略，该策略克服了这些限制。以CuF为例，原位形成的O-烷基异脲加合物的活化可实现有效的亲核氟转移至一系列伯醇和仲醇。已通过光谱研究探究了CuF反应活性增强的根源。还展示了该方法在实现F放射性标记方面的实用性。
