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A modular flow reactor for performing Curtius rearrangements as a continuous flow process.

Marcus Baumann1, Ian R Baxendale, Steven V Ley

  • 1Innovative Technology Centre, Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, UK.

Organic & Biomolecular Chemistry
|April 19, 2008
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Summary

A mesofluidic flow reactor enables efficient Curtius rearrangement of carboxylic acids. This method allows for the in-situ trapping of reactive isocyanate intermediates with diverse nucleophiles.

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Area of Science:

  • Organic Chemistry
  • Chemical Engineering
  • Reaction Engineering

Background:

  • The Curtius rearrangement is a valuable organic reaction for synthesizing amines and related compounds.
  • Traditional batch methods for Curtius rearrangement can involve hazardous intermediates and require careful control.
  • Flow chemistry offers potential advantages in safety, efficiency, and scalability for such transformations.

Purpose of the Study:

  • To investigate the application of a mesofluidic flow reactor for conducting Curtius rearrangement reactions.
  • To explore the in-situ trapping of isocyanate intermediates generated during the rearrangement.
  • To demonstrate the compatibility of the flow system with various nucleophiles for diverse product synthesis.

Main Methods:

  • Utilized a mesofluidic flow reactor system.
  • Carboxylic acids were reacted with diphenylphosphoryl azide to initiate the Curtius rearrangement.
  • Intermediate isocyanates were trapped in-situ using a range of nucleophiles (e.g., alcohols, amines).

Main Results:

  • Successfully performed Curtius rearrangement in a continuous flow mesoreactor.
  • Demonstrated efficient in-situ trapping of isocyanate intermediates.
  • Obtained various amine and carbamate derivatives with good yields.

Conclusions:

  • Mesofluidic flow reactors are suitable for safe and efficient execution of Curtius rearrangement.
  • The flow system facilitates the generation and immediate utilization of reactive isocyanates.
  • This approach offers a versatile platform for synthesizing diverse organic molecules.