title: Palladium-Catalyzed, Enantioselective α-Arylation of α-Fluorooxindoles.
abstract: Transition-metal-catalyzed asymmetric α-arylation of carbonyl compounds is a widely studied method for C-C bond formation. Recently, the α-arylation of α-fluoro ketones has been reported, including enantioselective α-arylation of α-fluoro ketones. However, the asymmetric α-arylation of α-fluoro carbonyl compounds in the carboxylic acid oxidation state has not been reported. We report the enantioselective α-arylation of α-fluorooxindoles with aryl triflates. The reaction occurs in high yield and with high enantioselectivity when catalyzed by a Pd-Segphos complex. This general class of product serves as an enantioenriched, nonenolizable version of α-aryl oxindoles.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Yushu
authors.initials: Y
authors.lastname: Jin
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Ming
authors.initials: M
authors.lastname: Chen
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Shaozhong
authors.initials: S
authors.lastname: Ge
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: John F
authors.identifier: 0000-0002-4157-468X
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D002384:Catalysis; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000078183:Oxindoles / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D008698:Mesylates; D000078183:Oxindoles; D010165:Palladium; C012077:trifluoromethanesulfonic acid