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

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

2.4K
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...
2.4K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.6K
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...
3.6K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

3.8K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.8K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

4.7K
Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
4.7K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

3.2K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
3.2K

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Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
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ダイアゾー化剤を使用する機能スクリーンのためのモジュール式クリック化学ライブラリ

Genyi Meng1, Taijie Guo1, Tiancheng Ma1

  • 1Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of the Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, China.

Nature
|October 4, 2019
PubMed
まとめ

この研究は,豊富な原始アミンからアジドを合成するための安全で実用的な方法を紹介しています. この突破は,特に銅 ((I) 触媒によるアジド-アルキンサイクル添加反応の範囲を拡大する.

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Identification of Small Molecule-binding Proteins in a Native Cellular Environment by Live-cell Photoaffinity Labeling
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Identification of Small Molecule-binding Proteins in a Native Cellular Environment by Live-cell Photoaffinity Labeling

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科学分野:

  • 有機化学
  • 化学生物学
  • 材料科学

背景:

  • クリック化学は,望ましい性質を持つ分子の迅速なモジュール合成を可能にします.
  • 銅 (I) 触媒によるアジド-アルキンサイクル添加 (CuAAC) と硫黄 (VI) フッ化物交換 (SuFEx) は鍵となるクリック反応である.
  • CuAAC反応は,アジド反応剤の毒性と爆発性によって制限されます.

研究 の 目的:

  • 原始アミンからアジドを合成するための安全で実用的な方法を開発する.
  • クリック化学の応用のためのアジド反応剤のアクセシビリティを拡大する.
  • 様々な科学分野におけるCuAAC反応の有用性を高めること.

主な方法:

  • フロロスルフリルアジド (FSO2N3) を用いて一次アミンをアジドに変換する新しい反応.
  • 96穴のプレートを使用して,1,200以上のアジドの高通量合成.
  • 反応の安全性と実用性の実証

主要な成果:

  • 主要なアミンからアジドを大量に合成した.
  • 信頼性の高い安全なアジド製法が確立された.
  • この新しい方法は,広く使用されているCuAAC反応と互換性があります.

結論:

  • 開発された方法は,アクセシブルなアジドと1,2,3-トリアゾールの範囲を大幅に拡大します.
  • この進歩は 有機合成,医薬品化学,材料科学に強力なツールを提供します.
  • この反応の安全性と効率性により,様々な研究分野に高度に適用できます.