A Sterically Tuned Directing Auxiliary Promotes Catalytic 1,2‐Carbofluorination of Alkenyl Carbonyl Compounds**
Zhonglin Liu, Lucas J. Oxtoby, Juntao Sun, Zi‐Qi Li, Nana Kim, Geraint H. M. Davies, Keary M. Engle
Abstract
Abstract 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.
Topics & Concepts
Steric effectsRegioselectivityCatalysisChemistryDenticityPalladiumArylCombinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCrystal structureAlkylFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions