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Updated: Mar 6, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Palladium-Catalyzed, Enantioselective α-Arylation of α-Fluorooxindoles
Yushu Jin1, Ming Chen1, Shaozhong Ge1
1Department of Chemistry, University of California , Berkeley, California 94720, United States.
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.
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