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Related Concept Videos

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.7K
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...
2.7K
Preparation of Amides01:29

Preparation of Amides

3.2K
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...
3.2K
Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

5.9K
Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α carbon to...
5.9K
Amides to Carboxylic Acids: Hydrolysis01:28

Amides to Carboxylic Acids: Hydrolysis

3.5K
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires severe conditions.
Acid-catalyzed hydrolysis:
Hydrolysis of amides under acidic conditions yields carboxylic acids. Since the reaction occurs slowly, hydrolysis requires the conditions of heat.
The mechanism begins with the protonation of the carbonyl oxygen by the acid catalyst. The protonation makes the amide carbonyl carbon more...
3.5K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

5.1K
Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
5.1K
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

6.5K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
6.5K

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Updated: Sep 16, 2025

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

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Electrochemically Chemoselective N-C(O) Bond Activation for Amide Esterification.

Xinxin Zhao1, Jian Wang1, Huaisong Hu1

  • 1School of Chemistry and Pharmacy Engineering, Nanyang Normal University, Nanyang, China, 473061.

Organic Letters
|July 9, 2025
PubMed
Summary

This study introduces an electrochemical method for direct esterification of primary amides using O-based nucleophiles. The sustainable process offers a new way for amide activation and late-stage functionalization in organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Methodology

Background:

  • Amide N-C(O) bond activation is challenging due to resonance stabilization.
  • Developing efficient methods for amide functionalization is crucial in organic synthesis.

Purpose of the Study:

  • To develop a novel electrochemical method for direct esterification of primary amides.
  • To provide a sustainable and efficient protocol for amide activation and modification.

Main Methods:

  • Electrochemical direct esterification of primary amides with O-based nucleophiles.
  • Utilized tetrabutylammonium bromide (TBAB) as a facilitator.
  • Conducted reactions under mild, open-to-air conditions.

Main Results:

  • Achieved direct esterification of primary amides with O-based nucleophiles.
  • Demonstrated excellent functional group tolerance and applicability in late-stage modification.
  • Mechanistic studies revealed in situ N-bromobenzamide formation and hydrogen-bond-assisted nucleophilic attack.

Conclusions:

  • The developed electrochemical method provides a practical and scalable alternative for amide activation and esterification.
  • This strategy offers a sustainable approach to synthesizing esters from amides.
  • The protocol's mild conditions and broad functional group tolerance make it valuable for complex molecule synthesis.