title: Palladium-catalyzed allylic fluorination of cinnamyl phosphorothioate esters.
abstract: A highly regioselective, Pd-catalyzed allylic fluorination of phosphorothioate esters is reported. This chemistry addresses several limitations of previously reported methods in which elimination and lack of reactivity were problematic. Preliminary mechanistic investigations reveal that these reactions are stereospecific and provide fluorinated products with net retention of stereochemical configuration. In analogy to other Pd-catalyzed allylic substitution reactions, this process likely proceeds through a palladium π-allyl intermediate.
authors.affiliation: Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.
authors.forename: Andrew M
authors.initials: AM
authors.lastname: Lauer
authors.forename: Jimmy
authors.initials: J
authors.lastname: Wu
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D002934:Cinnamates / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D054879:Halogenation; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010766:Phosphorylation; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D002934:Cinnamates; D004952:Esters; D005609:Free Radicals; D013438:Sulfhydryl Compounds; C029010:cinnamic acid; D010165:Palladium