A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis

The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and N-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitated by a transient directing group. The synthetically enabling methodology constructs vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities, forging products that map onto bioactive compounds.

Automated summary

The study reports a new method facilitated by a transient directing group for the vicinal fluorofunctionalization of alkenes, leading to the construction of vicinal stereocenters with excellent selectivity.