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Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating.

M Erdélyi1, A Gogoll

  • 1Department of Organic Chemistry, Uppsala University, Box 531, 751 21 Uppsala, Sweden. mate@kemi.uu.se

The Journal of Organic Chemistry
|June 9, 2001
PubMed
Summary

A new microwave-assisted Sonogashira reaction offers rapid and efficient coupling of diverse aryl and heteroaryl compounds with trimethylsilylacetylene. This optimized method achieves excellent yields in minutes, showcasing its broad applicability in organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • The Sonogashira reaction is a vital cross-coupling method for forming carbon-carbon bonds.
  • Traditional Sonogashira protocols can be time-consuming and require specific conditions.

Purpose of the Study:

  • To develop a microwave-enhanced, rapid, and efficient homogeneous Sonogashira reaction.
  • To expand the substrate scope for Sonogashira coupling, including challenging aryl chlorides and heterocycles.

Main Methods:

  • Microwave irradiation was employed to accelerate the homogeneous-phase Sonogashira coupling.
  • The reaction was tested with various aryl halides (iodides, bromides, triflates, chlorides) and heteroaryl derivatives.
  • Trimethylsilylacetylene was used as the alkyne coupling partner.

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Main Results:

  • The developed method demonstrated excellent yields (80-95%) across a wide range of substrates.
  • Reaction times were significantly reduced, ranging from 5 to 25 minutes.
  • The protocol proved effective for substrates with diverse substituents and heteroaromatic systems like pyridine and thiophene.

Conclusions:

  • Microwave enhancement provides a rapid and efficient pathway for the Sonogashira reaction.
  • The optimized homogeneous-phase protocol is versatile, accommodating various aryl and heteroaryl halides.
  • This method offers a valuable tool for efficient synthesis of alkynylated compounds.