There are many methods to introduce fluorine into organic compounds, but not all of them can be handled easily and safely in ordinary organic chemistry laboratories. Versatile and frequently used amine/HF reagents are Et3N.3HF, Pyr.9HF (Olah’s reagent), and similar combinations. Different selectivity of such reagents was observed in nucleophilic substitution reactions of bromides, mesylates, tosylates, etc. by fluoride at sp3 hybridized carbon centers. Moreover, activated C-H bonds can be substituted by fluoride using different oxidizers in combination with the mentioned fluorinating reagents. Particularly, regio- and stereoselectivity of ring opening reactions of epoxides are very much depending on the nature of the epoxide and the reagent. Similarly, the outcome of halofluorination reactions and related transformations can be controlled by the combination of the electrophile and the fluoride source.

Selectivity of different amine/HF reagents for synthesis of functionalized organic fluorine compounds

2019 Spring National Meeting

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