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A 2018 study ranked the kinetic reactivity of 10 commonly used electrophilic N–F fluorinating reagents using a shared set of 1,3-dicarbonyl model substrates. The reported rates span eight orders of magnitude. The scale can help guide reagent choice when the intended reaction resembles the measured chemistry, but it is not a universal ranking for every substrate or condition.
What the reactivity scale measures
In electrophilic fluorination, a carbon nucleophile reacts with an N–F electrophile to form a new carbon–fluorine bond. The researchers measured how quickly selected N–F reagents fluorinated a common set of 1,3-dicarbonyl model substrates, then used those kinetics to compare reagent reactivity. Chemistry World reported the study by David Hodgson of Durham University and colleagues as spanning eight orders of magnitude across the 10 reagents (Chemistry World, 8 October 2018). The associated paper by N. Rozatian and colleagues appeared in Chemical Science in 2018 (DOI: 10.1039/c8sc03596b).
That breadth means reagent choice can substantially affect reaction rate within the tested framework. It does not mean the study tested every fluorinating reagent, or that its order predicts outcomes for every nucleophile, solvent, or reaction setup. The reported comparison is kinetic: it concerns measured rates, not a universal measure of how strongly a reagent can fluorinate.
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How to use the ranking when choosing a reagent
Treat the scale as a starting point if your substrate and reaction resemble the 1,3-dicarbonyl chemistry used to obtain it. A rate comparison from one model system is not, by itself, a prediction of yield, selectivity, or compatibility for a different substrate.
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- Match the reaction class: prioritize kinetic evidence when the intended transformation and conditions resemble those measured.
- Check substrate scope and selectivity: the model-substrate scale does not establish which position will fluorinate, or how well a different nucleophile will react.
- Consider handling and stability: reagent power is only one practical consideration. A 2021 review discusses thermal stability and non-hygroscopic behavior as relevant properties, alongside potential handling limitations of highly powerful reagents (Beilstein Journal of Organic Chemistry review, 2021).
- Confirm the mechanism: electrophilic N–F transfer and radical fluorination are different reaction modes; data relevant to one should not be treated as a ranking for the other.
The review identifies N-fluoropyridinium derivatives, N-fluorobenzenesulfonimide (NFSI), and Selectfluor among recognizable N–F reagent classes in kinetic fluorination work. It also reports that Selectfluor, NFSI, and N-fluoropyridinium salt derivatives are made commercially on a large scale. Those literature observations do not establish current local availability or pricing.
Why other measures of fluorinating power are not interchangeable
A kinetic reactivity scale answers how quickly a reaction proceeded under a specified set of measured conditions. Other quantitative measures answer different questions. The 2021 review distinguishes kinetic scales from calculated Fluorine Plus Detachment (FPD) energy and N–F homolytic bond-dissociation energy (Beilstein Journal of Organic Chemistry review, 2021). FPD energy is a thermodynamic descriptor; bond-dissociation energy is relevant to homolytic bond cleavage and radical chemistry. Neither can be substituted directly for a measured rate of electrophilic fluorination.
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The available report identifies the scale’s size and scope but does not provide a complete reagent-by-reagent ordering or all numerical rate constants. Accordingly, the useful conclusion is the scale’s measured breadth and reaction-specific nature—not an inferred order assembled from partial information.
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