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<p>Rearrangement reactions are generally considered to be a rapid and synergistic intramolecular reconstructing process that is insensitive to intermolecular intruders. We report that α-iminol rearrangements could be strategically redirected by the interception of Petasis reactions, in the context of being avoided by strong electron-withdrawing groups on the migrative aryl units. 1,4-Aryl migration prevails over 1,2-aryl migration via forming a boron-ate complex. By leveraging this reactivity, we developed a regiospecific synthesis of unsymmetrically 2,3-diaryl substituted indoles from three readily available feedstocks: an amine, an arylglyoxal, and a boronic acid. While traditional Petasis reactions with similar three-component inputs are typically applied to build C(sp<sup>3</sup>)-C(sp<sup>2</sup>) and C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bonds, the present transformation offers a special opportunity for constructing a C(sp<sup>2</sup>)-C(sp<sup>2</sup>) linkage. Highly substituted indole motifs with structural diversity in the C2 position are easily accessed by this three-component reaction. A mechanism containing a copper-cobalt collaborative promotion process was suggested.</p>

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Intercepting an avoided α-iminol rearrangement with a Petasis reaction for the synthesis of 2,3-diaryl substituted indoles

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  • 发表日期：

    2025年5月15日

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  • Hui-Min Zhu,
  • Tong Lei,
  • Zhi-Xin Liao,
  • Jia-Chen Xiang,
  • An-Xin Wu

摘要

Rearrangement reactions are generally considered to be a rapid and synergistic intramolecular reconstructing process that is insensitive to intermolecular intruders. We report that α-iminol rearrangements could be strategically redirected by the interception of Petasis reactions, in the context of being avoided by strong electron-withdrawing groups on the migrative aryl units. 1,4-Aryl migration prevails over 1,2-aryl migration via forming a boron-ate complex. By leveraging this reactivity, we developed a regiospecific synthesis of unsymmetrically 2,3-diaryl substituted indoles from three readily available feedstocks: an amine, an arylglyoxal, and a boronic acid. While traditional Petasis reactions with similar three-component inputs are typically applied to build C(sp3)-C(sp2) and C(sp3)-C(sp3) bonds, the present transformation offers a special opportunity for constructing a C(sp2)-C(sp2) linkage. Highly substituted indole motifs with structural diversity in the C2 position are easily accessed by this three-component reaction. A mechanism containing a copper-cobalt collaborative promotion process was suggested.