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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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Recent Advances in the Pauson-Khand Reaction.

J David Ricker1, Laina M Geary1

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

Topics in Catalysis
|October 24, 2017
PubMed
Summary

The Pauson-Khand reaction, a [2+2+1] cycloaddition, has seen recent advances in catalytic and asymmetric methods. This review covers new developments in regioselectivity and substrate scope for this important organic synthesis reaction.

Keywords:
Pauson-Khand reactionsasymmetric catalysistransition metal catalyzed cycloadditions

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • The Pauson-Khand reaction is a [2+2+1] cycloaddition involving alkynes, alkenes, and carbon monoxide.
  • This reaction has been a significant area of research for over four decades.

Purpose of the Study:

  • To review recent advancements in the Pauson-Khand reaction.
  • To highlight catalytic and asymmetric variants of the reaction.
  • To discuss improvements in regioselectivity and substrate scope.

Main Methods:

  • Literature review of recent publications on the Pauson-Khand reaction.
  • Focus on catalytic and asymmetric methodologies.
  • Analysis of regioselectivity and substrate scope.

Main Results:

  • Significant progress has been made in developing efficient catalytic systems for the Pauson-Khand reaction.
  • Novel asymmetric variants have been established, enabling enantioselective synthesis.
  • Expanded substrate scope and improved control over regioselectivity have been achieved.

Conclusions:

  • The Pauson-Khand reaction continues to be a powerful tool in organic synthesis.
  • Recent developments have enhanced its utility, particularly through catalytic and asymmetric approaches.
  • Further research promises even broader applications in complex molecule synthesis.