Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1313509 | Journal of Fluorine Chemistry | 2016 | 9 Pages |
•A set of new chiral sulfonamide-pyridine ligands has been synthesized from a new chiral sulfoxide.•The Pd/sulfonamide-pyridine ligand catalyst provided the monofluorinated allylic products with high ee.•The sulfonamide moiety on the ligand has a significant effect on the enantiocontrol.
Chiral o-aniline sulfoxides serving as chiral sulfurous source were synthesized, from which new sulfonamide-pyridine ligands were made in three-steps. These compounds proved to be efficient S,N-ligands for enantiocontrol of palladium-catalyzed allylic substitutions of dimethyl 2-fluoromalonate. The induced effect of the Pd/S,N-ligand catalyst on the enantioselectivity depends on the steric demand of the substituent on the sulfoxide moiety. This method provided the fluorine-containing allylic products with up to 94% ee.