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

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 interactio...

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Bibliographic Details
Published in:Organic letters 2017-05, Vol.19 (10), p.2572-2575
Main Authors: Mizuta, Satoshi, Otaki, Hiroki, Kitagawa, Ayako, Kitamura, Kanami, Morii, Yuki, Ishihara, Jun, Nishi, Kodai, Hashimoto, Ryo, Usui, Toshiya, Chiba, Kenya
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00887