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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

7.2K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
7.3K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.6K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.6K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

5.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
5.0K
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)

4.6K
Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
4.6K
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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置換ヘテロ芳香族化合物へのインドリン-3-オン部分の位置選択的導入

Andrew J Daszczynski1, Nina Bui1, F G West1

  • 1Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.

The Journal of organic chemistry
|December 22, 2025
PubMed
まとめ
この要約は機械生成です。

新しいデュアル触媒法は、C2置換インドリン-3-オンを効率的に合成します。このアプローチは、生体分子の選択的な官能化のための反応性C-アシルイミン中間体を利用し、合成化学を拡張します。

キーワード:
インドリン-3-オンデュアル触媒C-アシルイミン位置選択的生体分子後期官能化合成化学

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科学分野:

  • 有機化学
  • 触媒
  • 合成方法論

背景:

  • C2置換インドリン-3-オンは価値のある複素環式化合物です。
  • 既存の合成法は効率または広範な適用性に欠ける可能性があります。

研究 の 目的:

  • C2置換インドリン-3-オンを合成するための穏やかで効率的なデュアル触媒法を開発すること。
  • 生成されたC-アシルイミン中間体の範囲と選択性を調査すること。
  • これらの方法の有用性を生体分子の後期官能化に実証すること。

主な方法:

  • 反応性のC-アシルイミン種をin situで生成するためにデュアル触媒システムが採用されました。
  • C-アシルイミン中間体は、様々な求核性アレーンによって傍受されました。
  • C-アシルイミンの選択性を評価するために、競合実験が実施されました。
  • この方法は、メラトニン、保護アミノ酸、およびジペプチドの官能化に適用されました。

主要な成果:

  • デュアル触媒法は、穏やかな条件下でC2置換インドリン-3-オンを形成することに成功しました。
  • C-アシルイミン中間体は、最も反応性の高い部位がブロックされている場合でも、アレーンによる位置選択的な捕捉を示しました。
  • ピロールは、テストされた他の複素環よりも好ましいヘテロ環式トラップとして特定されました。
  • メラトニン、アミノ酸、およびジペプチドの後期官能化が達成され、方法の可能性を示しました。

結論:

  • C2置換インドリン-3-オン合成のための新規かつ穏やかなデュアル触媒戦略が確立されました。
  • C-アシルイミン中間体は、有用な反応性と選択性のプロファイルを示します。
  • この方法論は、複雑な生体分子の後期多様化のための貴重なツールを提供します。