Ionic Liquid-Mediated Hydrofluorination of <i>o</i>-Azaxylylenes Derived from 3-Bromooxindoles

Abstract

The hydrofluorination reaction of 3-bromooxindole using mild HF reagents in an ionic liquid is described. This transformation can operate at room temperature to give a series of 3-substituted 3-fluorooxindole derivatives including racemic BMS 204352 (MaxiPost). The mechanistic study about interactions between HF and 3-butyl-1-methylimidazolium tetrafluoroborate [bmim][BF₄] is also discussed on the basis of energy calculations.