Abstract
Fluoroolefins, which play an increasingly important role as peptide
mimics in pharmaceuticals and as crop protection agents, are generated
using a fluoro-Julia-Kocienski olefination. Their preparation
can easily be accomplished using a Mitsunobu reaction and subsequent
oxidation to generate the required benzothiazolyl sulfones. The
key step of this process was the electrophilic α-fluorination
of the sulfone with N -fluorobenzenesulfonimide.
The last stage of the successful synthesis of the fluoroolefins
was the modified Julia-Kocienski olefination under basic
conditions. Further functionalization was followed with the application
of a Suzuki reaction.
Key words
fluorine - olefination - sulfones - heterocycles - cross-coupling
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