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Issue 46, 2018
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A quantitative reactivity scale for electrophilic fluorinating reagents

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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 CH3CN. 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.

Graphical abstract: A quantitative reactivity scale for electrophilic fluorinating reagents

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Supplementary files

Article information


Submitted
13 Aug 2018
Accepted
13 Sep 2018
First published
14 Sep 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 8692-8702
Article type
Edge Article

A quantitative reactivity scale for electrophilic fluorinating reagents

N. Rozatian, I. W. Ashworth, G. Sandford and D. R. W. Hodgson, Chem. Sci., 2018, 9, 8692
DOI: 10.1039/C8SC03596B

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    [Original citation] - Published by The Royal Society of Chemistry.

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