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Related Concept Videos

Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

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The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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

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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.’
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Carbocations02:10

Carbocations

15.1K
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.9K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

4.4K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

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The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
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Updated: Apr 18, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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A novel aromatic carbocation-based coupling reagent for esterification and amidation reactions.

Thanh V Nguyen1, Demelza J M Lyons

  • 1Department of Chemistry, Curtin University, Perth, WA 6102, Australia. thanhvinh.nguyen@curtin.edu.au.

Chemical Communications (Cambridge, England)
|January 21, 2015
PubMed
Summary

A new tropylium-based reagent enables efficient synthesis of esters, amides, lactones, and peptides. This catalytic method offers a mild and effective approach for carboxylic acid coupling reactions.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Carboxylic acid derivatives are crucial in pharmaceuticals and materials science.
  • Mild and efficient coupling methods are essential for complex molecule synthesis.

Purpose of the Study:

  • To develop a novel tropylium-based coupling reagent.
  • To establish a mild and efficient method for synthesizing esters, amides, lactones, and peptides.

Main Methods:

  • Development of a tropylium-based coupling reagent.
  • Application of the reagent in various nucleophilic coupling reactions.
  • Utilizing the reagent in catalytic amounts with a sacrificial agent.

Main Results:

  • Successful synthesis of diverse esters, amides, lactones, and peptides.
  • Demonstration of mild reaction conditions.
  • Proof of concept for catalytic application with a sacrificial reagent.

Conclusions:

  • A novel tropylium-based reagent provides an efficient synthetic route.
  • The catalytic approach offers a sustainable and effective method for carboxylic acid functionalization.