Publication details for Dr David R.W. HodgsonRozatian, Neshat, Ashworth, Ian W., Sandford, Graham & Hodgson, David R. W. (2018). A Quantitative Reactivity Scale for Electrophilic Fluorinating Reagents. Chemical Science 9(46): 8692-8702.
- Publication type: Journal Article
- ISSN/ISBN: 2041-6520 (print), 2041-6539 (electronic)
- DOI: 10.1039/C8SC03596B
- Further publication details on publisher web site
- Durham Research Online (DRO) - may include full text
Author(s) from Durham
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.