Regioselective Difunctionalization of 2,6-Difluorophenols Triggered by Sigmatropic Dearomatization

• Okamoto, Koichi

  Department of Chemistry, Graduate School of Science, Kyoto University

• Nogi, Keisuke

  Department of Chemistry, Graduate School of Science, Kyoto University

• Yorimitsu, Hideki

  Department of Chemistry, Graduate School of Science, Kyoto University

Abstract

Regioselective difunctionalization of 2, 6-difluorophenols with aryl sulfoxides and nucleophiles has been accomplished. The reaction is composed of (1) Pummerer-based [3, 3] sigmatropic dearomatization to generate 2, 4-cyclohexadienone, (2) Michael addition of a nucleophile, and (3) liberation of HF for rearomatization. Besides the [3, 3] rearrangement, [2, 3] sigmatropic rearrangement from sulfonium ylide generated from alkyl sulfoxide promotes the dearomatization, resulting in installation of α-sulfanylalkyl group.

Journal

• Organic Letters

  Organic Letters 22 (14), 5540-5544, 2020-07-17

  American Chemical Society (ACS)

Keywords

• Organic Chemistry
• Physical and Theoretical Chemistry
• Biochemistry

Details

• CRID: 1051693803362876288
• NII Article ID: 120006895436
• ISSN: 15237060
• ISSN: 15237052
• DOI: 10.1021/acs.orglett.0c01904
• HANDLE: 2433/255853
• Web Site: https://pubs.acs.org/doi/pdf/10.1021/acs.orglett.0c01904
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • Crossref
  • CiNii Articles
  • KAKEN