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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.
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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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Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
16.4K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
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,...
2.2K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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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.
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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Updated: Sep 8, 2025

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Iodine(III) reagents for oxidative aromatic halogenation.

Luis A Segura-Quezada1, Karina R Torres-Carbajal1, Kevin A Juárez-Ornelas1

  • 1Universidad de Guanajuato, Departamento de Química, División de Ciencias Naturales y Exactas, Campus Guanajuato, Cerro de la Venada S/N, 36040, Guanajuato, Gto., Mexico. csolorio@ugto.mx.

Organic & Biomolecular Chemistry
|June 15, 2022
PubMed
Summary

Iodine(III) reagents offer a safe, green alternative for organic synthesis, enabling diverse functionalizations of aromatic and heteroaromatic compounds. This review highlights their use in introducing halogens and other groups, showcasing their versatility in modern chemistry.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Green Chemistry

Background:

  • Iodine(III) reagents are recognized for their safety, non-toxicity, and ease of handling.
  • They serve as effective alternatives to hazardous reagents and harsh reaction conditions in organic synthesis.
  • Their oxidizing properties are valuable for modifying various chemical structures.

Purpose of the Study:

  • To review representative procedures utilizing iodine(III) reagents for functionalizing aryl and heteroaryl compounds.
  • To emphasize the introduction of halogens and other non-aromatic groups.
  • To showcase the versatility and green aspects of iodine(III) chemistry.

Main Methods:

  • Literature review of developed procedures involving iodine(III) reagents.
  • Focus on metal-free transformations and functionalization strategies.
  • Analysis of halogen introduction into aromatic and heteroaromatic systems.

Main Results:

  • Iodine(III) reagents facilitate the functionalization of diverse aromatic and heteroaromatic cores.
  • Successful introduction of halogens and other non-aromatic groups has been demonstrated.
  • Metal-free arylation and other transformations are well-documented.

Conclusions:

  • Iodine(III) reagents are versatile, safe, and green tools in organic synthesis.
  • They provide efficient methods for halogenation and other functionalizations of (hetero)aromatic systems.
  • Their application represents a significant advancement over traditional hazardous methods.