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Synlett 1997; 1997(6): 655-656
DOI: 10.1055/s-1997-3272
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Highly Regioselective Anodic Monofluorination of Oxindole and 3-Oxo-1,2,3,4-tetrahydroisoquinoline Derivatives

Yankun Hou, Seiichiro Higashiya, Toshio Fuchigami*
  • *Department of Electronic Chemistry, Tokyo Institute of Technology, Midori-ku, Yokohama 226, Japan, Fax +81 45 921 1089; E-mail fuchi@echem.titech.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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Highly regioselective monofluorination of 1-phenyl-3-(phenylthio)oxindole (1a), (1-(p-tolyl)-3-(phenylthio)-5-methyloxindole (1b) was successfully carried out using Me4NF•4HF as a supporting electrolyte to provide the corresponding 3-fluorinated products in 64% and 50% yields, respectively. Similarly, 2-benzyl-3-oxo-4-(phenylthio)-1,2,3,4-tetrahydroisoquinoline (1c) was also selectively fluorinated with Et4NF•3HF to give the 4-fluorinated product in 71% yield.

oxindole - tetrahydroisoquinoline - electrochemical fluorination - anodic oxidation - regioselectivity

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