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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.4K
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.
6.4K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

2.9K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
2.9K
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

3.1K
Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
3.1K
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

5.7K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
5.7K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

6.3K
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...
6.3K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

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

2.0K
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...
2.0K

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関連する実験動画

Updated: Sep 10, 2025

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

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ピリジンを含む電荷移転複合体によって触媒化された脱炭素化フッ素化

Zhiyang Ma1, Liang Zhang1, Jinglan Wen1

  • 1Institute of Green Chemistry and Molecular Engineering, GBRCE for Functional Molecular Engineering, Lehn Institute of Functional Materials, School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, China.

Organic letters
|August 20, 2025
PubMed
まとめ

新しい有機フォトレドックスシステムは,ピリジン-セレクトフローア複合体を使用して,可視光駆動によるカルボキシル酸のデカルボキシル化フローリネーションを行う. この方法は様々なアルキルカルボキシル酸を 有価なフッ素化合物に効率的に変換する.

さらに関連する動画

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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関連する実験動画

Last Updated: Sep 10, 2025

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
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Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
14:11

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

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科学分野:

  • 有機化学
  • フォトレドックス触媒
  • 化化学

背景:

  • 脱炭化反応は,C−C結合の形成と機能化に不可欠である.
  • フォトレドックス触媒は 可視光を用いた有機変異に 持続可能なアプローチを提供します
  • 選択的フッ素化は合成化学における重要な課題である.

研究 の 目的:

  • アルキルカルボキシル酸の化のための新しいフォトレドックス脱炭素化システムを開発する.
  • 反応性を高めるための触媒として電荷移転複合体を利用する.
  • 様々な炭酸基板に適用できる可視光媒介プロトコルを確立する.

主な方法:

  • ピリジン誘導体とセレクトフローアの間の電荷伝送複合体の形成.
  • 基本条件下で可視光で照射する.
  • 主要な,二次的,三次的なアルキルカルボキシル酸に適用する.

主要な成果:

  • アルキルカルボキシル酸のデカルボキシル化フッ化が成功しました.
  • 主要な,二次的,三次的な基板を含む,良好な基板の範囲を示した.
  • この新しい触媒システムは 温和な環境下でも効率的に動作します

結論:

  • 開発された有機フォトレドックスシステムは,デカルボキシル化フッ素化のための効果的な経路を提供します.
  • カルボキシル酸を活性化するためのユニークな戦略を提供します.
  • この方法論は,有機分子にフッ素を導入するためのツールキットを拡張します.