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Related Concept Videos

Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

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Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

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

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The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
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Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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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-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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Oxidation-Reduction Reactions03:11

Oxidation-Reduction Reactions

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Oxidation–Reduction Reactions
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Related Experiment Video

Updated: Jan 21, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Iridium-Catalyzed Reductive Allylation of Esters.

Lan-Gui Xie1, Jack Rogers1, Ioannis Anastasiou1

  • 1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, U.K.

Organic Letters
|August 10, 2019
PubMed
Summary

This study introduces a new iridium-catalyzed method for converting carboxylic esters into α-branched ethers. The process uses hydrosilylation and Lewis acid activation to create valuable ether derivatives from various esters.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carboxylic esters are versatile starting materials in organic synthesis.
  • Developing efficient methods for functionalizing esters remains a key challenge.
  • α-branched ethers are important structural motifs in pharmaceuticals and natural products.

Purpose of the Study:

  • To develop a novel catalytic reductive transformation of carboxylic esters into α-branched ethers.
  • To establish a chemoselective method for synthesizing valuable ether derivatives.
  • To explore the utility of the method in constructing heterocyclic frameworks.

Main Methods:

  • Iridium-catalyzed hydrosilylation of ester and lactone functionalities.
  • Formation of silyl acetal intermediates.
  • Lewis acid-mediated generation of oxocarbenium ions.
  • Nucleophilic interception with allyltributyltin.

Main Results:

  • Successful synthesis of α-branched alkyl-alkyl ethers from various carboxylic esters.
  • Demonstrated chemoselectivity for ethyl over tert-butyl esters.
  • Efficient construction of pyrrolidine, piperidine, and azepane rings via downstream manipulation of amino acid-derived products.

Conclusions:

  • The developed iridium-catalyzed reductive allylation provides a powerful new route to α-branched ethers.
  • The method offers good functional group tolerance and chemoselectivity.
  • This approach enables the synthesis of valuable heterocyclic compounds from readily available starting materials.