Lawrence Berkeley National Laboratory
Palladium-Catalyzed, Enantioselective α-Arylation of α-Fluorooxindoles.
- Author(s): Jin, Yushu
- Chen, Ming
- Ge, Shaozhong
- Hartwig, John F
- et al.
Published Web Locationhttps://doi.org/10.1021/acs.orglett.7b00294
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.