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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Efficient isocyanide-less isocyanide-based multicomponent reactions.

Constantinos G Neochoritis1, Silvia Stotani1, Bhupendra Mishra1

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Summary

A novel isocyanide-less multicomponent reaction (IMCR) offers a safer alternative to traditional methods. This innovative approach avoids hazardous isocyanides, paving the way for greener organic chemistry practices.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Isocyanides are versatile reagents in organic synthesis.
  • However, isocyanides are known for their noxious odor and toxicity.
  • Existing isocyanide-based multicomponent reactions (IMCRs) pose significant handling challenges.

Purpose of the Study:

  • To develop a safer and more accessible alternative to traditional isocyanide-based multicomponent reactions.
  • To create an isocyanide-less protocol that retains the synthetic utility of IMCRs.
  • To provide a greener approach to complex molecule synthesis.

Main Methods:

  • Development of a novel synthetic protocol that circumvents the direct use of isocyanides.
  • Application of the new method to established multicomponent reaction frameworks.
  • Characterization of reaction products and optimization of conditions.

Main Results:

  • Successfully established an isocyanide-less multicomponent reaction (IMCR).
  • The new protocol demonstrates broad applicability and efficiency.
  • Avoidance of hazardous isocyanide intermediates significantly improves safety and ease of use.

Conclusions:

  • The developed isocyanide-less IMCR represents a significant advancement in synthetic organic chemistry.
  • This method offers a practical and environmentally benign alternative to conventional isocyanide chemistry.
  • The protocol has the potential to replace older methods in various synthetic applications.