C−F Arylation of Polyfluorophenols by Means of Sigmatropic Dearomatization/Defluorination Sequence

• Okamoto, Koichi

  Department of Chemistry, Graduate School of Science, Kyoto University

• Nogi, Keisuke

  Department of Chemistry, Graduate School of Science, Kyoto University

• Shimokawa, Jun

  Department of Chemistry, Graduate School of Science, Kyoto University

• Yorimitsu, Hideki

  Department of Chemistry, Graduate School of Science, Kyoto University

Abstract

Selective C−F arylation of polyfluorophenols with aryl sulfoxides has been accomplished by means of a sigmatropic dearomatization/defluorination sequence. This sequence consists of three processes: 1) interrupted Pummerer reaction to form S−O‐tethered sulfonium salt; 2) C−C‐forming [3, 3] sigmatropic rearrangement with dearomatization; and 3) Zn‐mediated defluorinative rearomatization. The present biaryl construction provides a facile access to polyfluorinated biaryls that is difficult to synthesize by other methods. The synthetic utility of the strategy is clearly demonstrated by the synthesis of a fluorinated analogue of Maxipost, a potassium channel modulator.

Journal

• Chemistry - A European Journal

  Chemistry - A European Journal 26 5615-5618, 2020-05-04

  Wiley

Keywords

• biaryls
• C−F transformation
• interrupted Pummerer reaction
• sigmatropic rearrangement
• synthetic methods

Details

• CRID: 1051412328386165248
• NII Article ID: 120006895437
• ISSN: 09476539
• ISSN: 15213765
• DOI: 10.1002/chem.202001158
• HANDLE: 2433/255854
• Web Site: https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fchem.202001158
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.202001158
• Web Site: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/chem.202001158
• Web Site: https://chemistry-europe.onlinelibrary.wiley.com/doi/am-pdf/10.1002/chem.202001158
• Text Lang: en
• Article Type: journal article
• Data Source:
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  • CiNii Articles
  • KAKEN