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α-Halogenation of Carboxylic Acid Derivatives: Overview

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...

Base-Promoted α-Halogenation of Aldehydes and Ketones

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...

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...

Halogenation of Alkenes

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.

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.

Reactions at the Benzylic Position: Halogenation

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.

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Updated: May 13, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphos^Ph Complexes

Published on: April 10, 2015

Decarbonylative halogenation by a vanadium complex.

Sujoy Rana¹, Rameezul Haque, Ganji Santosh

¹Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.

Inorganic Chemistry

|March 6, 2013

Summary

Researchers developed a novel metal-mediated decarbonylative halogenation reaction. This new method utilizes a divanadium complex for C-H bond functionalization, offering a unique approach to chemical synthesis.

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Last Updated: May 13, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

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Published on: April 10, 2015

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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Published on: May 26, 2019

Area of Science:

Organometallic Chemistry
Catalysis
Synthetic Chemistry

Background:

Metal-catalyzed C-H bond halogenation and aldehyde decarbonylation are established reactions.
Metal-mediated decarbonylative halogenation has not been previously reported.

Purpose of the Study:

To develop the first metal-mediated decarbonylative halogenation reaction.
To explore a novel synthetic pathway using a divanadium complex.

Main Methods:

Utilized a divanadium oxoperoxo complex K3V(5+)2(O2(2-))4(O(2-))2(μ-OH) (1).
Investigated the reaction mechanism through experimental observations.

Main Results:

Successfully demonstrated the first metal-mediated decarbonylative halogenation.
Proposed a concerted reaction mechanism for the transformation.

Conclusions:

The developed method offers a new route for decarbonylative halogenation.
The study expands the scope of metal-mediated organic reactions.