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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.3K
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...
3.3K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.2K
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...
2.2K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

11.3K
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.
11.3K
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

2.5K
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.
2.5K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

5.0K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
5.0K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.3K
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.
4.3K

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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1つのダイアゾ化合物から2つの銅カルベン

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
PubMed
まとめ

研究者らは,ダイアゾアセタミドの脱炭素化によって形成された新しい銅カルベンの複合体を発見した. カーベンのリガンドのこの予期せぬ変化は,過渡金属による有機合成における以前の仮定に異議を唱える.

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Last Updated: Nov 12, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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科学分野:

  • 有機金属化学
  • 有機合成
  • カタリシス

背景:

  • 移行金属複合物は,有機合成のためのダイアゾ化合物から金属カルベンを生成するために広く使用されます.
  • 以前は,金属カルベンのカルベン断片は,母体ダイアゾ化合物から変化しないと考えられていた.

研究 の 目的:

  • 銅複合体とディアゾアセタミドの反応を調査する.
  • 結果として生じる銅カルベンの種を特徴づけ,反応機構を理解する.

主な方法:

  • TpMsCu ((THF) とN,N-ディエチルディアゾアセタミドの反応
  • 銅カルベンの単離と特徴付け
  • 実験データ分析,密度関数理論 (DFT) 計算,およびマイクロキネティックモデリング.

主要な成果:

  • 安定した単体置換された銅カルベンの分離,TpMsCuC ((H) ((NEt2),脱炭素化による.
  • TpMsCu ((CO) として閉じ込められた一酸化炭素の検出
  • 予想されるカルベンの TpMsCuC ((H)) ((CONEt2) の形成と,COの損失によるその後の変換の証拠.

結論:

  • この研究は,脱炭素化によって生じる金属-カルベンの複合体における改変カルベンのリガンドの最初の例を報告している.
  • COの損失を含む提案されたメカニズムは,観察された改変した銅カルベンの形成を説明する.
  • この発見は,金属カルベンの反応性の理解を広げ,新しい合成の可能性を提供します.