Synthesis 2016; 48(23): 4099-4109
DOI: 10.1055/s-0035-1562532
paper
© Georg Thieme Verlag Stuttgart · New York

Controlled Generation of 3-Triflyloxyarynes

Authors

  • Keisuke Uchida

    Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan   Email: s-yoshida.cb@tmd.ac.jp   Email: thosoya.cb@tmd.ac.jp
  • Suguru Yoshida*

    Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan   Email: s-yoshida.cb@tmd.ac.jp   Email: thosoya.cb@tmd.ac.jp
  • Takamitsu Hosoya*

    Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan   Email: s-yoshida.cb@tmd.ac.jp   Email: thosoya.cb@tmd.ac.jp
Further Information

Publication History

Received: 25 June 2016

Accepted after revision: 15 July 2016

Publication Date:
24 August 2016 (online)


Graphical Abstract

Abstract

The efficient generation of 3-triflyloxyarynes, including those bearing a transformable group, through an iodine–magnesium exchange reaction of 1,3-bis(triflyloxy)-2-iodoarenes was achieved by using finely tuned reaction conditions that efficiently suppressed the competing thia-Fries rearrangement. The method enabled the facile synthesis of a wide range of multisubstituted arenes.

Supporting Information