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Mechanism + Description

CPyFluor serves to activate the alcohol in the presence of base through the formation of the intermediate pyridinesulfonate, which can subsequently be displaced with fluoride.

General comments

PyFluor represents a low-cost deoxyfluorination reagent that exhibits high chemical and thermal stability. The reagent has been demonstrated to tolerate a wide range of functionality, and minimize competing elimination reactions, which often complicate purifications of deoxyfluorination processes. Reaction times are longer and require basic conditions, though the relative ease of preparation coupled with the enhanced safety profile of the reagent should enable the use of this methodology on scale.

Key references

Nielson, M. K.; Ugaz, C. R.; Li, W.; Doyle, A. G. PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent. J. Am. Chem. Soc. 2015, 137, 9571-9574.

Hu, W.-L.; Hu, X.-G.; Hunter, L. Recent Developments in the Deoxyfluorination of Alcohols and Phenols: New Reagents, Mechanistic Insights, and Applications. Synthesis 2017, 49, 4917-4930.


Relevant scale up examples

None found.