Electrochemical Synthesis of Hetero[7]helicenes Containing Pyrrole and Furan Rings <i>via</i> an Oxidative Heterocoupling and Dehydrative Cyclization Sequence

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  • Mohamed S. H. Salem
    SANKEN Osaka University Ibaraki-shi Osaka 567-0047 Japan
  • Md. Imrul Khalid
    SANKEN Osaka University Ibaraki-shi Osaka 567-0047 Japan
  • Makoto Sako
    Graduate School of Pharmaceutical Sciences Osaka University Suita-shi Osaka 565-0871 Japan
  • Keigo Higashida
    SANKEN Osaka University Ibaraki-shi Osaka 567-0047 Japan
  • Charlie Lacroix
    Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), CNRS-UMR 8182 Laboratoire de Catalyse Moléculaire Université Paris-Saclay 91405 Orsay Cedex France
  • Masaru Kondo
    Department of Materials Science and Engineering Graduate School of Science and Engineering Ibaraki University Hitachi-shi Ibaraki 316-8511 Japan
  • Ryo Takishima
    Department of Applied Chemistry Graduate School of Engineering Osaka University Suita-shi Osaka 565-0871 Japan
  • Taisei Taniguchi
    Department of Applied Chemistry Graduate School of Engineering Osaka University Suita-shi Osaka 565-0871 Japan
  • Masahiro Miura
    Innovative Catalysis Science Division Institute for Open and Transdisciplinary Research Initiatives (ICS-OTRI) Osaka University Suita-shi Osaka 565-0871 Japan
  • Giang Vo‐Thanh
    Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), CNRS-UMR 8182 Laboratoire de Catalyse Moléculaire Université Paris-Saclay 91405 Orsay Cedex France
  • Hiroaki Sasai
    SANKEN Osaka University Ibaraki-shi Osaka 567-0047 Japan
  • Shinobu Takizawa
    SANKEN Osaka University Ibaraki-shi Osaka 567-0047 Japan

抄録

<jats:title>Abstract</jats:title><jats:p>The electrochemical synthesis of hetero[7]helicenes including pyrrole and furan rings has been established. A single electrochemical operation led to an oxidative heterocoupling and dehydrative cyclization sequence to afford oxaza[7]helicenes in 50–86% yields with 45–77% Faradic efficiencies. Their derivatization and chiroptical properties were also investigated.</jats:p><jats:p><jats:boxed-text content-type="graphic" position="anchor"><jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" mimetype="image/png" position="anchor" specific-use="enlarged-web-image" xlink:href="graphic/adsc202201262-toc-0001-m.png"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text> </jats:p>

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