A Sterically Tuned Directing Auxiliary Promotes Catalytic 1, 2‐Carbofluorination of Alkenyl Carbonyl Compounds. (15th December 2022)

• Record Type: Journal Article
• Authors: Liu, Zhonglin; Oxtoby, Lucas J.; Sun, Juntao; Li, Zi‐Qi; Kim, Nana; Davies, Geraint H. M.; Engle, Keary M.
• Is Part Of: Angewandte Chemie. Volume 135:Number 4(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-15
• Subjects: Alkene Functionalization -- Cross-Coupling -- Directing Group -- Fluorination -- Palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202214153
• Languages: English
• ISSNs: 0044-8249

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. Abstract : Judicious tuning of the steric environment on the bidentate directing auxiliary is proposed to facilitate challenging C(sp 3 )−F reductive elimination from a Pd IV intermediate in the site‐selective palladium‐catalyzed three‐component coupling of unactivated alkenyl carbonyl compounds, aryl‐ or alkenylboronic acids, and N ‐fluorobenzenesulfonimide.