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Acid-Catalyzed Ring-Opening of Epoxides

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...

Base-Catalyzed Ring-Opening of Epoxides

Base-Catalyzed Ring-Opening of Epoxides

Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...

Base-Catalyzed Aldol Addition Reaction

Base-Catalyzed Aldol Addition Reaction

As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.

Acid-Catalyzed Dehydration of Alcohols to Alkenes

Acid-Catalyzed Dehydration of Alcohols to Alkenes

In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.

Acid-Catalyzed Aldol Addition Reaction

Acid-Catalyzed Aldol Addition Reaction

The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.

Acid-Catalyzed Hydration of Alkenes

Acid-Catalyzed Hydration of Alkenes

Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.

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Updated: Feb 6, 2026

Gyroid Nickel Nanostructures from Diblock Copolymer Supramolecules

Gyroid Nickel Nanostructures from Diblock Copolymer Supramolecules

Published on: April 28, 2014

Carboiodination Catalyzed by Nickel.

Hyung Yoon¹, Austin D Marchese¹, Mark Lautens¹

¹Davenport Research Laboratories, Department of Chemistry , University of Toronto , Toronto , Ontario M5S 3H6 , Canada.

Journal of the American Chemical Society

|August 24, 2018

Summary

A new nickel-catalyzed reaction efficiently creates nitrogen heterocycles from aryl bromides. This scalable method uses a dual ligand system for high yields and enantioselective synthesis.

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Synthesis of Platinum-nickel Nanowires and Optimization for Oxygen Reduction Performance

Synthesis of Platinum-nickel Nanowires and Optimization for Oxygen Reduction Performance

Published on: April 27, 2018

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Developing efficient synthetic routes for nitrogen-containing heterocycles is crucial in medicinal chemistry and materials science.
Existing methods often require harsh conditions or expensive catalysts, limiting their broad applicability.
Carbon-halogen bond preservation during cyclization is a significant challenge in organic synthesis.

Purpose of the Study:

To develop a novel nickel-catalyzed cycloisomerization reaction.
To achieve the formation of a new carbon-carbon bond while preserving the carbon-halogen bond.
To synthesize nitrogen-containing heterocycles with high yields and enantioselectivity using readily available starting materials.

Main Methods:

Employed a cost-effective and readily available nickel catalyst.
Utilized a rare dual ligand system, combining a bisphosphine and a bisphosphine monoxide.
Optimized reaction conditions for aryl bromides, including the addition of potassium iodide for subsequent alkyl iodide formation.

Main Results:

Successfully developed a nickel-catalyzed cycloisomerization reaction.
Achieved good to excellent yields of nitrogen-containing heterocycles.
Demonstrated the formation of enantioenriched products, showcasing the effectiveness of the dual ligand system.

Conclusions:

The developed nickel-catalyzed reaction provides a scalable and efficient route to valuable nitrogen heterocycles.
The method allows for the preservation of the carbon-halogen bond, enabling further synthetic transformations.
The use of a dual ligand system is key to achieving high enantioselectivity in this novel cycloisomerization.