1-Fluoro-3,3-dimethyl-1,2-benziodoxole (1) is a hypervalent iodine derivative developed by Stuart et al.1) This compound is stable to air and moisture and used as an electrophilic fluorinating reagent for a α-monofluorination of β-ketoesters in the presence of triethylamine trihydrofluoride. In this reaction, a difluorination reaction occurs by increasing the amounts of 1 with heating at 60 °C.
On the other hand, Szabó et al. have reported a difluorination reaction of 1 with styrene derivatives.2) They suggest that the reaction proceeds through the formation of a phenonium ion intermediate based on a deuterium-isotope-labelling experiment.
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An Air- and Moisture- stable Electrophilic Fluorinating Reagent
References
- 1) Electrophilic fluorination using a hypervalent iodine reagent derived from fluoride
- 2) Mild Silver-Mediated Geminal Difluorination of Styrenes Using an Air- and Moisture-Stable Fluoroiodane Reagent
