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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 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...

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...

Crossed Aldol Reactions: Overview

Crossed Aldol Reactions: Overview

Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

The reaction between two different carbonyl compounds comprising α hydrogen in the presence of a strong base like lithium diisopropylamide (LDA) to form a crossed aldol product is known as a directed aldol reaction. The directed aldol reaction is depicted in Figure 1.

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.

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Related Experiment Video

Updated: Oct 8, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Copper-Catalyzed Aldehyde Exchanged Amidation.

Lei-Yang Zhang¹, Nai-Xing Wang¹, Yue-Hua Wu¹

¹Technical Institute of Physics and Chemistry & University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190, China.

Organic Letters

|December 30, 2021

Summary

This summary is machine-generated.

Chemists synthesized novel secondary amides with aldehyde groups from various aldehydes and amines. This efficient method, yielding up to 89%, offers a new route to valuable chemical compounds.

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Last Updated: Oct 8, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Published on: June 21, 2017

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

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

Published on: May 26, 2019

Area of Science:

Organic Chemistry
Synthetic Chemistry
Catalysis

Background:

The synthesis of bioactive amides is a significant area of chemical research.
Developing efficient methods for incorporating functional groups into amides is crucial for creating new molecules.

Purpose of the Study:

To report the first synthesis of secondary amides bearing an aldehyde group.
To establish a versatile and efficient method for generating these novel amide compounds.

Main Methods:

Reaction of various (hetero)aryl and aliphatic aldehydes with secondary amines.
Utilized a Copper (Cu) catalytic system (Cu(I/II/III) cycle).
Employed high-resolution mass spectrometry to detect key reaction intermediates.

Main Results:

Successfully synthesized secondary amides containing an aldehyde group from over 40 examples of aldehydes.
Achieved moderate to excellent product yields, up to 89%.
Proposed and provided evidence for a reaction mechanism involving a Cu(I/II/III) catalytic cycle and radical rearrangement.

Conclusions:

A novel and efficient synthetic route to secondary amides with aldehyde functionalities has been developed.
The proposed catalytic cycle and radical rearrangement mechanism provide insight into the reaction pathway.
This method offers a valuable tool for accessing diverse amide-containing molecules for further chemical applications.