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

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

Org. Lett. 201719, 1390–1393.

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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