Vicinal

Chemistry

Selectivity

Ionic liquid

Palladium

Stereocenter

Organic chemistry

Catalysis

Enantioselective synthesis

Group (periodic table)

Combinatorial chemistry

Hexafluorophosphate

Journal of the American Chemical Society

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.

A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis