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Synlett 1998; 1998(9): 973-974
DOI: 10.1055/s-1998-5738
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Selective Anodic Fluorination of Flavones

Yankun Hou* , Seiichiro Higashiya, Toshio Fuchigami
  • *Department of Electronic Chemistry, Tokyo Institute of Technology, Midori-ku, Yokohama 226-8502, Japan; Fax + 81 45 924-5489; E-mail: fuchi@echem.titech.ac.jp
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Publication Date:
31 December 2000 (online)

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Anodic fluorination of flavone and 6-chloroflavone was carried out using Et3N ⋅ 3 HF and Et4NF ⋅ 4 HF as supporting electrolytes. The former supporting electrolyte provided 3-monofluorinated flavones 2 preferentially while the latter one gave 2,3-difluorinated flavones 3 predominantly. It was also found that the yields of 2 increased significantly at a higher temperature as 30 °C. Furthermore, it was confirmed that 2 was formed by dehydrofluorination of 3 with free Et3N in Et3N ⋅ 3 HF.

flavone - 6-chloroflavone - electrochemical fluorination - anodic oxidation - regioselectivity