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Related Concept Videos

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

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Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.
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Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

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Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
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Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

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Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
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α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

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Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the...
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Silver-catalyzed carboxylation.

K Sekine1, T Yamada1

  • 1Department of Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. yamada@chem.keio.ac.jp.

Chemical Society Reviews
|February 19, 2016
PubMed
Summary
This summary is machine-generated.

Silver catalysts enable efficient carboxylation and cyclization of alkyne derivatives using carbon dioxide. This review highlights recent advances in silver-catalyzed reactions for synthesizing valuable heterocyclic compounds and carboxylic acid derivatives.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Silver-catalyzed reactions are crucial in organic synthesis.
  • Recent advancements (since 2007) showcase novel applications of silver catalysts.
  • Carbon dioxide utilization is a key focus in sustainable chemistry.

Purpose of the Study:

  • To review recent studies on silver-catalyzed carboxylation reactions using carbon dioxide.
  • To highlight the synthesis of heterocyclic compounds and carboxylic acid derivatives.
  • To emphasize the mild reaction conditions and high reactivity of silver catalysts.

Main Methods:

  • Review of literature on silver-catalyzed carboxylation reactions.
  • Focus on sequential carboxylation and cyclization of alkyne derivatives (propargyl alcohols and amines).
  • Comparison of silver catalysts with other transition metals under mild conditions.

Main Results:

  • Silver catalysts exhibit significant reactivity for carboxylation and cyclization using CO2.
  • Mild reaction conditions are achieved, unlike with other transition metals.
  • Effective synthesis of heterocyclic compounds and carboxylic acid derivatives is demonstrated.

Conclusions:

  • Silver catalysis offers a promising route for the effective utilization of carbon dioxide in organic synthesis.
  • These methods provide efficient pathways to valuable heterocyclic and carboxylic acid derivatives.
  • The development of silver-catalyzed carboxylation reactions represents a significant advancement in green chemistry.