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 is proposed to facilitate challenging C(sp3)–F reductive elimination from a Pd(IV) intermediate to afford 1,2-carbofluorination products in good yields and with high regioselectivity.