Palladium-Catalyzed, Enantioselective α‑Arylation of α‑Fluorooxindoles

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.