4.8 Article

Ionic Liquid-Mediated Hydrofluorination of o-Azaxylylenes Derived from 3-Bromooxindoles

Journal

ORGANIC LETTERS
Volume 19, Issue 10, Pages 2572-2575

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b00887

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Funding

  1. Japan Society for Promotion of Science (JSPS) [26713041]
  2. Program of the network type Joint Usage/Research Center for Radiation Disaster Medical Science of Hiroshima University
  3. Fukushima Medical University
  4. Nagasaki University
  5. Grants-in-Aid for Scientific Research [15K07861, 26713041] Funding Source: KAKEN

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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-buty1-1-methylimidazolium tetrafluoroborate [bmim][BF4] is also discussed on the basis of energy calculations.

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