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A Quantitative Reactivity Scale for Electrophilic Fluorinating Reagents

Rozatian, Neshat; Ashworth, Ian W.; Sandford, Graham; Hodgson, David R.W.

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Neshat Rozatian

Ian W. Ashworth

Graham Sandford


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.


Rozatian, N., Ashworth, I. W., Sandford, G., & Hodgson, D. R. (2018). A Quantitative Reactivity Scale for Electrophilic Fluorinating Reagents. Chemical Science, 9(46), 8692-8702.

Journal Article Type Article
Acceptance Date Sep 13, 2018
Online Publication Date Sep 14, 2018
Publication Date Dec 14, 2018
Deposit Date Sep 14, 2018
Publicly Available Date Nov 29, 2018
Journal Chemical Science
Print ISSN 2041-6520
Electronic ISSN 2041-6539
Publisher Royal Society of Chemistry
Peer Reviewed Peer Reviewed
Volume 9
Issue 46
Pages 8692-8702


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