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Exploiting Continuous Processing for Challenging Diazo Transfer and Telescoped Copper-Catalyzed Asymmetric

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Flow chemistry enables safe and efficient synthesis of α-diazocarbonyl compounds using triflyl azide. This method allows direct use in subsequent enantioselective reactions without catalyst contamination.

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Area of Science:

  • Organic Chemistry
  • Flow Chemistry
  • Synthetic Methodology

Background:

  • Triflyl azide is a highly reactive reagent posing handling hazards.
  • Efficient synthesis of α-diazocarbonyl compounds is crucial for various organic transformations.
  • Existing diazo-transfer methods may have limitations in scope or safety.

Purpose of the Study:

  • To develop a safer and more efficient method for synthesizing α-diazocarbonyl compounds using triflyl azide in flow.
  • To demonstrate the compatibility of the flow-generated diazo compounds with subsequent enantioselective reactions.
  • To explore both Regitz-type and deacylative/debenzoylative diazo-transfer processes.

Main Methods:

  • Generation and in-situ use of triflyl azide in a continuous flow system.
  • Application of Regitz-type diazo transfer reactions.
  • Application of deacylative/debenzoylative diazo-transfer processes.
  • Telescoping the diazo-transfer with copper-catalyzed intramolecular aromatic addition and C-H insertion reactions.

Main Results:

  • Efficient synthesis of various α-diazocarbonyl compounds (ketones, amides, sulfonyl esters) in excellent yields.
  • Versatility in solvent choice for the diazo-transfer process.
  • Demonstrated safety improvement by avoiding isolation of triflyl azide.
  • Successful direct transfer of the crude reaction stream to immobilized copper bis(oxazoline) catalyst without loss of enantioselectivity.

Conclusions:

  • Flow generation and use of triflyl azide provide a safe and efficient route to α-diazocarbonyl compounds.
  • The developed flow process is compatible with subsequent highly enantioselective catalytic reactions.
  • This integrated flow approach enhances synthetic efficiency and safety in organic synthesis.