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Lewis Acid-Promoted Typical Friedel-Crafts Reactions Using DMSO as a Carbon Source.

Nagaraju Vodnala1, Sanjay Singh1, Chinmoy Kumar Hazra1

  • 1Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India.

The Journal of Organic Chemistry
|July 20, 2022
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Summary

Researchers developed a new method for synthesizing diarylmethanes (DAMs) using dimethyl sulfoxide (DMSO) as both solvent and carbon source. This efficient protocol yields functionalized DAMs, including precursors for anti-cancer and anticoagulant drugs.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Diarylmethanes (DAMs) are important structural motifs in pharmaceuticals and materials.
  • Efficient and mild synthetic routes for DAMs are highly sought after.
  • Existing methods often require harsh conditions or expensive reagents.

Purpose of the Study:

  • To develop a novel, mild, and efficient synthetic protocol for diarylmethanes (DAMs).
  • To utilize dimethyl sulfoxide (DMSO) as a C1 source and solvent.
  • To demonstrate the versatility of the method through synthesis of functionalized DAMs and bioactive compounds.

Main Methods:

  • Employing DMSO as a C1 source and solvent.
  • Utilizing trifluoromethanesulfonic acid trimethylsilyl ester (TMSOTf) as a Lewis acid promoter.
  • Reacting aromatic compounds under mild conditions.

Main Results:

  • High yields of symmetrical and unsymmetrical diarylmethanes (DAMs) were achieved.
  • DMSO demonstrated a dual role as solvent and C1 source.
  • Deuterated DMSO (DMSO-d6) enabled incorporation of a -CD2 moiety.
  • The protocol was successfully applied to synthesize precursors for anti-breast cancer and anticoagulant agents.

Conclusions:

  • A mild, efficient, and versatile synthetic protocol for diarylmethanes was established.
  • The dual role of DMSO simplifies the synthetic strategy.
  • The method offers a practical route to valuable pharmaceutical intermediates.