Neshat Rozatian
A Quantitative Reactivity Scale for Electrophilic Fluorinating Reagents
Rozatian, Neshat; Ashworth, Ian W.; Sandford, Graham; Hodgson, David R.W.
Authors
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.
Citation
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 | Mar 29, 2024 |
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 |
DOI | https://doi.org/10.1039/c8sc03596b |
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Publisher Licence URL
http://creativecommons.org/licenses/by/4.0/
Copyright Statement
This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
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