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Durham University

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Publication details for Dr David R.W. Hodgson

Rozatian, Neshat, Ashworth, Ian W., Sandford, Graham & Hodgson, David R. W. (2018). A Quantitative Reactivity Scale for Electrophilic Fluorinating Reagents. Chemical Science 9(46): 8692-8702.

Author(s) from Durham


Electrophilic N-F fluorination agents underpin the introduction of fluorine in aliphatic systems across drug and academic research. The choice of N-F reagent is currently determined through empirical experimentation in the absence of quantitative values for electrophilicities. Here we report an experimentally-determined kinetic reactivity scale for ten N-F fluorinating reagents, including Selectfluor™, NFSI, Synfluor™ and several N-fluoropyridinium salts, in acetonitrile. The reactivity scale, which covers eight orders of magnitude, employs para-substituted 1,3-diaryl-1,3-dicarbonyl derivatives to measure relative and absolute rate constants. The para-substituted 1,3-diaryl-1,3-dicarbonyl scaffold delivers a convenient, sensitive spectrophotometric reporter of reactivity that also led to the discovery of a unique form of tautomeric polymorphism.