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Open Access Publications from the University of California

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

  • Author(s): Jin, Yushu
  • Chen, Ming
  • Ge, Shaozhong
  • Hartwig, John F
  • et al.

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.

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