Solvent-Controlled Leaving-Group Selectivity in Aromatic Nucleophilic Substitution

  • Lukas Hintermann
    Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan
  • Ritsuki Masuo
    Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan
  • Keisuke Suzuki
    Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551, Japan

書誌事項

公開日
2008-10-09
DOI
  • 10.1021/ol801962a
公開者
American Chemical Society (ACS)

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説明

A solvent-controlled inversion of leaving group ability allows selective access to either of two internal substitution products in S(N)Ar reactions of substrates with competing leaving groups. Application of this principle in a selective synthesis of the highly functionalized xanthone core of the antibiotic FD-594 is presented.

収録刊行物

  • Organic Letters

    Organic Letters 10 (21), 4859-4862, 2008-10-09

    American Chemical Society (ACS)

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