A quantitative reactivity scale for electrophilic fluorinating reagents.

Chem Sci

Chemistry Department , Durham University, South Road , Durham , DH1 3LE , UK . Email:

Published: December 2018

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 -fluoropyridinium salts, in CHCN. The reactivity scale, which covers eight orders of magnitude, employs -substituted 1,3-diaryl-1,3-dicarbonyl derivatives to measure relative and absolute rate constants. The -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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6263395PMC
http://dx.doi.org/10.1039/c8sc03596bDOI Listing

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