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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.

Multiple Halogenation of Methyl Ketones: Haloform Reaction

Multiple Halogenation of Methyl Ketones: Haloform Reaction

A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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...

Formation of Halohydrin from Alkenes

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.

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...

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Related Experiment Video

Updated: May 28, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Ortho-Carborane-Derived Halogen Bonding Organocatalysts.

Christoph J Vonnemann¹, Elric Engelage¹, Jas S Ward²

¹Fakultät für Biochemie und Chemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801, Bochum, Germany.

Angewandte Chemie (International Ed. in English)

|February 14, 2025

Summary

New iodinated ortho-carborane catalysts exhibit strong halogen bonding and superior Lewis acidity. These novel catalysts effectively perform halide abstraction and catalyze challenging nitro-Michael additions, expanding the scope of organocatalysis.

Keywords:

calorimetry halogen bonding noncovalent interactions organocatalysis ortho-carboranes

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

Area of Science:

Organometallic Chemistry
Supramolecular Chemistry
Catalysis

Background:

Halogen bonding (XB) is a non-covalent interaction crucial in various chemical processes.
Traditional halogen bond donors often face limitations in Lewis acidity and scope.
Icosahedral carboranes offer a unique scaffold for designing novel XB catalysts.

Purpose of the Study:

To introduce and characterize novel multidentate neutral halogen bonding catalysts based on iodinated icosahedral ortho-carborane moieties.
To evaluate the Lewis acidity and binding capabilities of these new catalysts.
To demonstrate the catalytic activity of these carborane-based catalysts in challenging organic transformations.

Main Methods:

Co-crystallization studies to determine structural interactions.
Calorimetric measurements to quantify binding enthalpies.
Proton Nuclear Magnetic Resonance (¹H NMR) titrations for binding analysis.
Quantum-chemical calculations to understand electronic properties and Lewis acidity.
Testing in halide abstraction and nitro-Michael addition reactions.

Main Results:

The iodocarborane catalysts demonstrated strong binding affinities towards halides and neutral compounds.
Superior Lewis acidity was observed compared to traditional perfluorinated halogen-bond donors.
The catalysts successfully outperformed existing donors in a halide abstraction reaction.
Catalytic activity was achieved in a nitro-Michael addition reaction, a transformation previously inaccessible for neutral XB organocatalysts.

Conclusions:

Multidentate neutral iodinated ortho-carborane moieties represent a powerful new class of halogen bonding catalysts.
These catalysts exhibit enhanced Lewis acidity and binding strength, surpassing conventional XB donors.
The developed catalysts enable challenging organic reactions, broadening the applications of neutral halogen bonding in organocatalysis.