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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

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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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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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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Updated: Nov 12, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Two Copper-Carbenes from One Diazo Compound.

María Álvarez1, Maria Besora2,3, Francisco Molina1

  • 1Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, 21007 Huelva, Spain.

Journal of the American Chemical Society
|March 18, 2021
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Summary

Researchers discovered a novel copper carbene complex formed via decarbonylation of a diazoacetamide. This unexpected modification of the carbene ligand challenges previous assumptions in transition-metal catalyzed organic synthesis.

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Area of Science:

  • Organometallic Chemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Transition-metal complexes are widely used to generate metal-carbenes from diazo compounds for organic synthesis.
  • Previously, the carbene fragment in metal-carbenes was believed to remain unchanged from the parent diazo compound.

Purpose of the Study:

  • To investigate the reaction of a copper complex with a diazoacetamide.
  • To characterize the resulting copper carbene species and understand the reaction mechanism.

Main Methods:

  • Reaction of TpMsCu(THF) with N,N-diethyl diazoacetamide.
  • Isolation and characterization of copper carbene products.
  • Experimental data analysis, Density Functional Theory (DFT) calculations, and microkinetic modeling.

Main Results:

  • Isolation of a stable monosubstituted copper carbene, TpMsCu═C(H)(NEt2), resulting from decarbonylation.
  • Detection of carbon monoxide trapped as TpMsCu(CO).
  • Evidence for the formation of the expected carbene, TpMsCu═C(H)(CONEt2), and its subsequent transformation via CO loss.

Conclusions:

  • The study reports the first instance of a modified carbene ligand in a metal-carbene complex, arising from decarbonylation.
  • A proposed mechanism involving CO loss explains the formation of the observed modified copper carbene.
  • This finding expands the understanding of metal-carbene reactivity and offers new synthetic possibilities.