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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

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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

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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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Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

Preparation of SNS CobaltII Pincer Model Complexes of Liver Alcohol Dehydrogenase

Published on: March 19, 2020

Cobalt-catalyzed

Jiao-Na Han¹, Cong Du¹, Xinju Zhu¹

¹College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, People's Republic of China.

Beilstein Journal of Organic Chemistry

|September 12, 2018

Summary

This summary is machine-generated.

Cobalt catalysis enables efficient synthesis of aryl ethers from 1-naphthylamine derivatives. This method tolerates various secondary alcohols and yields biologically relevant fluorine-aryl ethers under mild conditions.

Keywords:

1-naphthylamines C–H activation alkoxylation cobalt catalysis secondary alcohols

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Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Aryl ethers are important structural motifs in pharmaceuticals and materials.
Efficient and selective synthesis of functionalized aryl ethers remains a challenge.
Direct C-H functionalization offers a more atom-economical approach to C-O bond formation.

Purpose of the Study:

To develop a novel cobalt-catalyzed method for C(sp2)-H alkoxylation of 1-naphthylamine derivatives.
To explore the scope and limitations of the developed catalytic system.
To synthesize biologically relevant fluorine-aryl ethers.

Main Methods:

Cobalt-catalyzed direct C(sp2)-H alkoxylation using 1-naphthylamine derivatives and various secondary alcohols.
Optimization of reaction conditions including catalyst loading, solvent, and temperature.
Removal of the directing group to afford the final aryl ether products.

Main Results:

Successful synthesis of aryl ethers with broad functional group tolerance.
Demonstrated tolerance of various secondary alcohols, including hexafluoroisopropanol, isopropanol, isobutanol, and isopentanol.
Obtained a series of biologically relevant fluorine-aryl ethers under mild reaction conditions.

Conclusions:

A novel and efficient cobalt-catalyzed C(sp2)-H alkoxylation of 1-naphthylamine derivatives has been established.
The developed method provides a facile route to synthesize diverse aryl ethers.
The methodology is particularly useful for accessing valuable fluorine-aryl ether compounds.