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Nitriles to Ketones: Grignard Reaction

Nitriles to Ketones: Grignard Reaction

Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles react with a Grignard reagent, followed by an aqueous acid, to yield ketones. The reaction introduces a new carbon–carbon bond. The alkyl–magnesium bond in the Grignard reagent is highly polar, so the alkyl carbon develops a carbanionic character and acts as a nucleophile.
The mechanism begins with a nucleophilic attack by the Grignard reagent...

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation

Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt condensation is...

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Ynamide-Mediated Ketone Synthesis.

Yibo Zhang¹, Jinfang Lv², Chunyu Han³

¹School of Pharmaceutical Sciences, Guangzhou Medical University, Guangzhou, Guangdong 511436, P. R. China.

Organic Letters

|May 12, 2026

Summary

This summary is machine-generated.

This study introduces a novel ynamide-mediated synthesis for ketones from carboxylic acids and Grignard reagents. The method efficiently forms carbon-carbon bonds under mild conditions, preserving stereochemistry for valuable peptidyl ketones.

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Published on: November 27, 2015

Area of Science:

Organic Chemistry
Synthetic Chemistry
Medicinal Chemistry

Background:

Ketone synthesis is crucial for organic chemistry.
Existing methods often require harsh conditions or multiple steps.
Developing efficient and mild synthetic routes is an ongoing challenge.

Purpose of the Study:

To develop a novel ynamide-mediated ketone synthesis.
To utilize readily available carboxylic acids and Grignard reagents.
To enable the synthesis of peptidyl ketones with high stereochemical integrity.

Main Methods:

Employing a nucleophilic attack of a C-nucleophile onto α-acyloxyenamides.
Utilizing a one-pot strategy for direct synthesis from carboxylic acids.
Applying the protocol to N-protected α-amino acids and peptidyl acids.

Main Results:

Achieved efficient C-C bond formation under mild conditions.
Demonstrated the practicality and generality of the one-pot strategy.
Successfully synthesized ketones from carboxylic acids without intermediate purification.
Retained stereochemical integrity in the synthesis of peptidyl ketones.

Conclusions:

The ynamide-mediated protocol offers a practical and efficient route to ketones.
This method is particularly valuable for synthesizing peptidyl ketones where chirality is critical.
The strategy enhances accessibility to complex ketone structures with preserved stereochemistry.