Facile Synthesis of Diverse <i>o</i>-Iodoaryl Triflates from <i>o</i>-Silylaryl Triflates by Aluminum-mediated Desilyliodination

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Author(s)

    • Yoshida Suguru
    • Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)
    • Hazama Yuki
    • Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)
    • Kanemoto Kazuya
    • Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)
    • Nakamura Yu
    • Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)
    • Hosoya Takamitsu
    • Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU)

Abstract

<p>A convenient method for preparing diverse <i>o</i>-iodoaryl triflates by the desilyliodination of <i>o</i>-silylaryl triflates has been developed. The treatment of <i>o</i>-silylaryl triflates with 1,3-diiodo-5,5-dimethylhydantoin (DIH) in the presence of aluminum trichloride efficiently afforded the corresponding <i>o</i>-iodoaryl triflates, including those with multiple 1-iodo-2-(triflyloxy)arene moieties. Various multisubstituted <i>o</i>-iodoaryl triflates were easily prepared by the iridium-catalyzed C–H borylation of readily available, simple <i>o</i>-silylaryl triflates, followed by deborylative transformations and subsequent desilyliodinaton.</p>

Journal

  • Chemistry Letters

    Chemistry Letters 48(7), 742-745, 2019

    The Chemical Society of Japan

Codes

  • NII Article ID (NAID)
    130007675010
  • Text Lang
    ENG
  • ISSN
    0366-7022
  • Data Source
    J-STAGE 
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