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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.

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.

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

Regioselectivity of Electrophilic Additions-Peroxide Effect

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

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...

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Updated: Sep 16, 2025

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

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Regioselective Halogenation at the γ-Position of β-Diketones Using Their BF₂ Complexes.

Kyosuke Kojima¹, Shunya Senda¹, Katsuhiko Ono¹

¹Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.

The Journal of Organic Chemistry

|July 8, 2025

Summary

Researchers regioselectively halogenated β-diketones using their BF2 complexes and N-halosuccinimide (NXS). This method yields versatile γ-halogenated β-diketones for applications in metal ligands and functional materials.

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Area of Science:

Organic Chemistry
Materials Science

Background:

β-diketones are versatile organic compounds with applications in coordination chemistry and materials science.
Regioselective functionalization of β-diketones is crucial for developing novel derivatives with tailored properties.

Purpose of the Study:

To develop a regioselective method for halogenating β-diketones at the γ-methyl groups.
To explore the utility of BF2 complexes of β-diketones in halogenation reactions.
To synthesize novel γ-halogenated β-diketones for potential applications.

Main Methods:

Formation of β-diketone BF2 complexes.
Regioselective γ-halogenation using N-halosuccinimide (NXS) in dichloromethane with catalytic triethylamine.
Hydrolysis of halogenated BF2 complexes to yield γ-halogenated β-diketones.

Main Results:

Successful regioselective halogenation of β-diketone BF2 complexes at the γ-methyl positions.
Formation of mono-, di-, and trihalogenated products controlled by NXS reactivity and BF2 complex structure.
Generation of diverse γ-halogenated β-diketones through a straightforward synthetic route.

Conclusions:

The BF2 complexation strategy enables efficient regioselective γ-halogenation of β-diketones.
The synthesized γ-halogenated β-diketones are valuable precursors for metal ligands and functional materials.
This method offers a new pathway for creating functionalized β-diketone derivatives.