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Hydroxamic Acids as Chemoselective (ortho-Amino)arylation Reagents via Sigmatropic Rearrangement.

Saad Shaaban1, Veronica Tona1, Bo Peng2

  • 1Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090, Wien, Austria.

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Hydroxamic acids enable metal-free ortho-aminoarylation of amides. This direct method efficiently attaches aniline residues to carbonyl compounds under mild conditions.

Keywords:
amidesaminoarylationchemoselectivityhydroxamic acidssigmatropic rearrangement

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Amide functionalization is crucial in organic synthesis.
  • Developing metal-free methods for C-N bond formation is highly desirable.

Purpose of the Study:

  • To describe a novel chemoselective ortho-aminoarylation of amides.
  • To utilize readily available hydroxamic acids as key reagents.

Main Methods:

  • Employing hydroxamic acids as reagents for amide arylation.
  • Conducting the reaction under metal-free and mild conditions.

Main Results:

  • Achieved chemoselective ortho-aminoarylation of amides.
  • Demonstrated a broad scope of substrate applicability.
  • Successfully attached aniline residues to carbonyl derivatives.

Conclusions:

  • Hydroxamic acids are effective reagents for metal-free amide arylation.
  • This method offers a direct and mild approach for synthesizing functionalized amides.