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A Radical-Based, Transition Metal-Free Approach for Diaryl Ketone Synthesis.

Dongjie Wang1, Jordan Garo2, Yinpeng Wang1

  • 1Département Chimie & Matériaux Moléculaire, Institut Charles Gerhardt de Montpellier, CNRS, ENSCM, University of Montpellier, 1919, route de Mende, 34293, Montpellier Cedex 5, France.

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Summary

A novel one-pot method synthesizes diaryl ketones using aryl halides and benzonitriles. This sustainable radical process avoids hazardous reagents, offering a greener alternative for chemical synthesis.

Keywords:
DFT calculationsdiaryl ketonesradical mechanismssustainable chemistrytransition metal‐free processes

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Green Chemistry

Background:

  • Diaryl ketones are crucial in pharmaceuticals, agrochemicals, and materials.
  • There is a growing demand for safer and more sustainable synthetic methods.

Purpose of the Study:

  • To develop a novel, straightforward, one-pot strategy for synthesizing diverse diaryl ketones.
  • To establish a sustainable and safe alternative to conventional synthetic approaches.

Main Methods:

  • A radical process involving the reaction of aryl halides with benzonitriles.
  • Utilized potassium tert-butoxide (KOtBu) and N,N-dimethylacetamide (DMA) as an organic reductant pair.
  • Employed air as the oxidant in a basic medium.

Main Results:

  • Successfully synthesized a broad array of diaryl ketones, including valuable target molecules.
  • The KOtBu/DMA system initiated the process via aryl radical generation.
  • Demonstrated a method free from corrosive reagents, toxic catalysts, peroxides, and carbon monoxide.

Conclusions:

  • The presented one-pot strategy offers a safe, sustainable, and efficient route to diaryl ketones.
  • This approach aligns with green chemistry principles, reducing environmental impact.
  • Provides a valuable alternative for academic and industrial synthesis of diaryl ketones.