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A quantitative reactivity scale for electrophilic fluorinating reagents.

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.

Abstract

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.

Item Type:Article
Full text:Publisher-imposed embargo
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Status:Peer-reviewed
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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