A Quantitative Reactivity Scale for Electrophilic Fluorinating Reagents
Rozatian, Neshat; Ashworth, Ian W.; Sandford, Graham; Hodgson, David R.W.
Ian W. Ashworth
Professor David Hodgson firstname.lastname@example.org
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. https://doi.org/10.1039/c8sc03596b
|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|
|Publisher||Royal Society of Chemistry|
|Peer Reviewed||Peer Reviewed|
Published Journal Article
Publisher Licence URL
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
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