Monofluorinated 5-membered rings via fluoromethylene transfer: synthesis of monofluorinated isoxazoline N-oxides

The synthesis of five-membered rings using fluoromethylene transfer chemistry is an attractive method for building fluorinated products of high value. This work demonstrates for the first time that one-fluorine-one-carbon modification of a substrate could be a viable strategy to access monofluorinated five-membered rings. The synthetic methodology was developed to access monofluorinated isoxazoline-N-oxides in one step starting from substituted 2-nitroacrylates using fluoromethylsulfonium reagents.

Automated summary

This study demonstrates a novel method for synthesizing five-membered rings using fluoromethylene transfer chemistry to produce fluorinated products of high value. The approach involves a one-step synthesis, utilizing one-fluorine-one-carbon modification of a substrate to access monofluorinated five-membered rings.