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Related Concept Videos

α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the electrophilic halogen to produce...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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.
Halogenation of Alkenes02:46

Halogenation of Alkenes

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.
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction at the stage of...
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.

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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Halogen-mediated C2/C3 functionalization of indoles: a concise overview.

Mariyaraj Arockiaraj1, Rojalini Nayak1, Venkatachalam Rajeshkumar1

  • 1Organic Synthesis & Catalysis Lab, Department of Chemistry, National Institute of Technology Warangal, Hanumakonda-506004, Telangana, India. rajeshv@nitw.ac.in.

Organic & Biomolecular Chemistry
|May 28, 2026
PubMed
Summary

This review details halogen-mediated functionalization of indoles, a key process in organic chemistry. It highlights methods using iodine, bromine, and N-halosuccinimides for sustainable synthesis of indole derivatives.

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Indole derivatives are crucial scaffolds in natural products and pharmaceuticals.
  • Sustainable and efficient synthesis of functionalized indoles is a growing research area.
  • Halogen-mediated functionalization offers a versatile route for indole modification.

Purpose of the Study:

  • To comprehensively review halogen-mediated functionalization strategies for indoles.
  • To emphasize the use of iodine, bromine, and N-halosuccinimides (NXS).
  • To discuss diverse bond-forming reactions and oxidative protocols.

Main Methods:

  • Electrophilic halogenation of indoles using molecular iodine, bromine, or NXS.
  • Subsequent functionalization via C-C, C-N, C-O, and C-S couplings.
  • Iodine-DMSO-mediated oxidative functionalization protocols.

Main Results:

  • Demonstrated versatility of halogenating agents for indole functionalization.
  • Systematic discussion of various bond-forming reactions on the indole scaffold.
  • Exploration of oxidative protocols for indole modification.

Conclusions:

  • Halogen-mediated strategies provide efficient and sustainable methods for indole functionalization.
  • The review serves as a resource for researchers in indole chemistry.
  • Diverse functional groups can be introduced onto indole derivatives using these methods.