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Related Concept Videos

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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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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β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

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Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds.  The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
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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...
4.3K
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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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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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Redox-Active Esters in Fe-Catalyzed C-C Coupling.

Fumihiko Toriyama1, Josep Cornella1, Laurin Wimmer1

  • 1Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society
|August 23, 2016
PubMed
Summary
This summary is machine-generated.

This study introduces novel iron-catalyzed cross-couplings of redox-active esters with organometallic reagents. This sustainable method offers advantages over traditional nickel catalysis for C-C bond formation.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Sustainable Chemistry

Background:

  • Decades of research exist on single electron transfer cross-couplings using nickel (Ni) and iron (Fe) catalysts with alkyl halides.
  • These methods are crucial for C-C bond formation in organic synthesis.

Purpose of the Study:

  • To demonstrate the first cross-coupling of redox-active esters with organozinc and organomagnesium species using an Fe catalyst.
  • To compare the efficacy of the Fe catalyst with a Ni catalyst for this transformation.

Main Methods:

  • Utilized an Fe-based catalyst system, initially developed for alkyl halides.
  • Coupled isolated and in situ derived redox-active esters with organozinc and organomagnesium reagents.
  • Performed a direct comparison with a Ni catalyst across diverse substrates.

Main Results:

  • Successfully achieved cross-couplings of redox-active esters with organometallic reagents using an Fe catalyst.
  • Demonstrated scalability and sustainability of the new Fe-catalyzed method.
  • Identified clear advantages of the Fe catalyst over the Ni catalyst in several cases.

Conclusions:

  • The developed Fe-catalyzed cross-coupling represents a significant advancement in C-C bond formation.
  • This method offers a sustainable and scalable alternative to existing Ni-catalyzed reactions.
  • The Fe catalyst shows promise for broader applications in organic synthesis.