Organic Letters
Organic Letters
5 years ago

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

Ionic Liquid-Mediated Hydrofluorination of o-Azaxylylenes Derived from 3-Bromooxindoles
Kanami Kitamura, Yuki Morii, Toshiya Usui, Hiroki Otaki, Ayako Kitagawa, Kodai Nishi, Kenya Chiba, Satoshi Mizuta, Jun Ishihara, Ryo Hashimoto
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00887

DOI: 10.1021/acs.orglett.7b00887

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