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Related Experiment Videos

Solid-phase synthesis of substituted alkynes using the Nicholas reaction.

Johan A Cassel1, Stefanie Leue, Natalie I Gachkova

  • 1Department of Organic Chemistry, Chalmers University of Technology, SE-412 96 Göteborg, Sweden. nina.kann@oc.chalmers.se

The Journal of Organic Chemistry
|December 21, 2002
PubMed
Summary

Researchers report the first solid-phase Nicholas reaction using cobalt complexes. This method efficiently forms carbon-oxygen or carbon-carbon bonds with polymer-bound alkynols and nucleophiles.

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Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Organometallic Chemistry

Background:

  • The Nicholas reaction is a valuable tool for carbon-carbon bond formation.
  • Solid-phase synthesis offers advantages in purification and reaction control.
  • Developing heterogeneous catalysts for organic reactions is an active area of research.

Purpose of the Study:

  • To report the first solid-phase Nicholas reaction.
  • To explore the use of polymer-bound cobalt complexes as catalysts.
  • To investigate the formation of C-O and C-C bonds using this methodology.

Main Methods:

  • Preparation of polymer-bound alkynols complexed with cobalt.
  • Reaction of these complexes with various nucleophiles in the presence of a Lewis acid.

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  • Analysis of reaction products to confirm bond formation.

    • Main Results:

    • Successful implementation of the Nicholas reaction on a solid support.
    • Demonstration of the formation of both carbon-oxygen and carbon-carbon bonds.
    • The polymer-bound cobalt complex acted as an effective catalyst.

    Conclusions:

    • The developed solid-phase Nicholas reaction provides a novel and efficient route for synthesizing complex organic molecules.
    • This approach simplifies purification and allows for potential catalyst recycling.
    • It expands the scope of the Nicholas reaction to solid-phase applications.