Rozatian, Neshat and Ashworth, Ian W. and Sandford, Graham and Hodgson, David R. W. (2018) 'A quantitative reactivity scale for electrophilic fluorinating reagents.', Chemical science., 9 (46). pp. 8692-8702.
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.
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|Publisher Web site:||https://doi.org/10.1039/C8SC03596B|
|Publisher statement:||This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.|
|Date accepted:||13 September 2018|
|Date deposited:||14 September 2018|
|Date of first online publication:||14 September 2018|
|Date first made open access:||29 November 2018|
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