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Related Concept Videos

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction00:56

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
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Ethyl Lithiodiazoacetate: Extremely Unstable Intermediate Handled Efficiently in Flow.

Simon T R Müller1, Tobias Hokamp1, Svenja Ehrmann1

  • 1School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff, CF10 3AT, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 25, 2016
PubMed
Summary
This summary is machine-generated.

Ethyl diazoacetate (EDA) can now be used with ketones via a continuous flow method. This new protocol overcomes rapid decomposition issues, enabling efficient synthesis of tertiary diazoalcohols.

Keywords:
diazo compoundsflow chemistryhazardous intermediateslithiation

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Flow Chemistry

Background:

  • Ethyl diazoacetate (EDA) is a versatile reagent in organic synthesis, commonly employed in metal-carbene reactions.
  • EDA can function as a nucleophile under basic conditions, but its application with carbonyl compounds beyond aldehydes often requires strong organometallic bases.
  • The intermediate ethyl lithiodiazoacetate is highly unstable and prone to rapid decomposition, limiting its synthetic utility.

Purpose of the Study:

  • To develop a robust continuous flow protocol for the reaction of ethyl lithiodiazoacetate with ketones.
  • To overcome the inherent instability and rapid decomposition of ethyl lithiodiazoacetate.
  • To provide direct access to tertiary diazoalcohols.

Main Methods:

  • Utilized a continuous flow reactor system to generate and immediately react ethyl lithiodiazoacetate.
  • Employed lithium diisopropylamide (LDA) as the base for deprotonation of EDA.
  • Investigated the addition of the in-situ generated ethyl lithiodiazoacetate to various ketone electrophiles.

Main Results:

  • Successfully implemented a continuous flow protocol for the nucleophilic addition of EDA to ketones.
  • Minimized the decomposition of the reactive ethyl lithiodiazoacetate intermediate through rapid processing.
  • Achieved good yields of tertiary diazoalcohols, demonstrating the efficiency of the flow method.

Conclusions:

  • The developed continuous flow protocol offers a practical solution for utilizing the nucleophilic potential of ethyl diazoacetate with ketones.
  • This method circumvents the decomposition challenges associated with ethyl lithiodiazoacetate, enabling its effective use in synthesis.
  • The protocol provides a valuable new route for the preparation of tertiary diazoalcohols.