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Organocatalytic Insertion of Isatins into Aryl Difluoronitromethyl Ketones

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journal contribution
posted on 29.12.2016, 00:00 by Ransheng Ding, Pegah R. Bakhshi, Christian Wolf
An organocatalytic method that achieves insertion of isatins into aryl difluoro­nitro­methyl ketones under mild conditions is described. The reaction occurs in the presence of 20 mol % of DBU and with 100% atom economy. A series of isatin derived difluoro­nitro­methyl substituted tertiary alcohol benzoates and naphthoates were prepared in 81–99% yield. The general synthetic usefulness of these 3-hydroxy­oxindole derivatives is demonstrated with the selective reduction to fluorooximes.