A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2‐Carbofluorination of Alkenyl Carbonyl Compounds**

The site‐selective palladium‐catalyzed three‐component coupling of unactivated alkenyl carbonyl compounds, aryl‐ or alkenylboronic acids, and N ‐fluorobenzenesulfonimide is described herein. Tuning of the steric environment on the bidentate directing auxiliary enhances regioselectivity and facilitates challenging C(sp 3 )−F reductive elimination from a Pd IV intermediate to afford 1,2‐carbofluorination products in moderate to good yields.