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Nitrous Oxide-Promoted Pauson-Khand Cycloadditions.

J David Ricker1, Vahid Mohammadrezaei1, Thomas J Crippen1

  • 1Department of Chemistry, University of Nevada, Reno, Reno, USA, 89557.

Organometallics
|August 1, 2019
PubMed
Summary

A novel Pauson-Khand cycladdition reaction using nitrous oxide as a promoter efficiently synthesizes cyclopentenones. This method avoids byproducts and uses readily available starting materials for improved yields.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry

Background:

  • The Pauson-Khand reaction is a vital tool for synthesizing cyclopentenones.
  • Traditional methods often involve harsh conditions or complex reagent preparation.

Purpose of the Study:

  • To develop a new, efficient Pauson-Khand cycladdition reaction.
  • To utilize nitrous oxide as a promoter for this transformation.

Main Methods:

  • A one-pot Pauson-Khand cycladdition of alkynes, alkenes, and carbon monoxide.
  • Cobalt carbonyl and nitrous oxide were used as promoters.
  • Equimolar amounts of reactants were employed, directly from the acetylenic component.

Main Results:

  • Cyclopentenones were successfully synthesized in good yields.
  • Nitrous oxide acted similarly to N-oxide promoters.
  • Terminal acetylenes and calcium carbide were suitable substrates.
  • Sequential [4+3] and [2+2+1] cycloadditions were achieved in two steps.

Conclusions:

  • This study presents an improved Pauson-Khand reaction using nitrous oxide.
  • The method offers advantages in terms of reagent simplicity and byproduct avoidance.
  • It provides a facile route to functionalized cyclopentenones from accessible precursors.