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Preparation of Amides01:29

Preparation of Amides

4.1K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
4.1K
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

4.3K
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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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.6K
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...
3.6K
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

4.7K
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...
4.7K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

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

20.9K
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.
20.9K
Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

3.9K
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.
3.9K

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

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Cobalt-Catalyzed Esterification of Amides.

Yann Bourne-Branchu1, Corinne Gosmini1, Grégory Danoun1

  • 1LCM, CNRS, Ecole Polytechnique, Université Paris-Saclay, 91128, Palaiseau Cedex, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 9, 2017
PubMed
Summary

This study introduces a novel cobalt-catalyzed method for activating N-Boc-amides and converting them into esters. This practical, efficient process operates under mild conditions without needing an inert atmosphere, using a cost-effective catalyst.

Keywords:
amidescobaltcross-couplingesterificationhomogeneous catalysis

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Amide activation is crucial for synthesizing various organic compounds.
  • Existing methods often require harsh conditions or expensive catalysts.
  • N-Boc-amides are common protecting groups in organic synthesis.

Purpose of the Study:

  • To develop a novel, practical, and efficient method for amide activation and ester formation.
  • To utilize an inexpensive and readily available cobalt catalyst.
  • To establish a catalytic system that operates under mild conditions and does not require an inert atmosphere.

Main Methods:

  • Cobalt-catalyzed amide activation of N-Boc-amides.
  • Conversion of activated amides to esters.
  • Optimization of reaction conditions, including catalyst loading and temperature.

Main Results:

  • The first reported cobalt-catalyzed amide activation of N-Boc-amides to esters.
  • High efficiency and broad substrate scope demonstrated.
  • Successful catalysis achieved with loadings as low as 1 mol%.
  • Mild reaction conditions and no requirement for an inert atmosphere.

Conclusions:

  • A new, practical, and cost-effective method for ester synthesis from N-Boc-amides has been developed.
  • The cobalt-catalyzed system offers a significant advancement in amide activation methodologies.
  • This approach provides a greener and more accessible route for organic synthesis.