Dehydrogenative Cycloisomerization/Arylation Sequence of<i>N</i>‐Propargyl Carboxamides with Arenes by Iodine(III)‐Catalysis

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  • Yuki Umakoshi
    Division of Applied Chemistry Institute of Engineering Tokyo University of Agriculture and Technology Koganei Tokyo 184-8588 Japan
  • Yusuke Takemoto
    Division of Applied Chemistry Institute of Engineering Tokyo University of Agriculture and Technology Koganei Tokyo 184-8588 Japan
  • Akira Tsubouchi
    Division of Applied Chemistry Institute of Engineering Tokyo University of Agriculture and Technology Koganei Tokyo 184-8588 Japan
  • Viktor V. Zhdankin
    Department of Chemistry and Biochemistry University of Minnesota Duluth MN 55812 USA
  • Akira Yoshimura
    Department of Chemistry and Biochemistry University of Minnesota Duluth MN 55812 USA
  • Akio Saito
    Division of Applied Chemistry Institute of Engineering Tokyo University of Agriculture and Technology Koganei Tokyo 184-8588 Japan

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<jats:title>Abstract</jats:title><jats:p>Dehydrogenative cycloisomerization/arylation sequence of heteroatom nucleophile‐tethered unactivated alkynes provides a facile and powerful approach to C−C bond formation between the generated heterocycles and unfunctionalized arenes. Here, we describe a hypervalent iodine(III)‐catalyzed synthesis of oxazoles concomitant with the introduction of aryl groups into side chain from<jats:italic>N</jats:italic>‐propargyl carboxamides and arenes, representing first C(<jats:italic>sp</jats:italic><jats:sup>3</jats:sup>)−C(<jats:italic>sp</jats:italic><jats:sup>2</jats:sup>) bond formation by the catalytic dehydrogenative cycloisomerization/arylation reaction in<jats:italic>exo‐dig</jats:italic>modes.</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/adsc202200219-toc-0001-m.png"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text></jats:p>

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