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Related Concept Videos

Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.9K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
4.9K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

4.2K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
4.2K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

3.2K
Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...
3.2K
Preparation of Amides01:29

Preparation of Amides

4.3K
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...
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Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

6.7K
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, secondary, and tertiary amides yield primary, secondary, and tertiary amines, respectively.
Amide reduction requires two equivalents of the reducing agent, acting as a source of hydride ions. As shown in the figure, the reaction is initiated with a nucleophilic attack by the hydride ion at the carbonyl carbon to form a tetrahedral intermediate.
6.7K
Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

4.1K
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.
4.1K

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Electrochemical Detection of Deuterium Kinetic Isotope Effect on Extracellular Electron Transport in Shewanella oneidensis MR-1
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Selective Deoxygenative Electroreduction of Amides.

Ying Hua1, En Luo1, Jie Liu1,2

  • 1College of Chemistry and Chemical Engineering, State Key Laboratory of Chemo and Biosensing, Hunan University, Changsha 410082, China.

Journal of the American Chemical Society
|March 30, 2026
PubMed
Summary

Researchers developed an efficient electroreduction method to convert unreactive amides into versatile amines. This novel process utilizes a zirconium catalyst and halosilane, avoiding hazardous reagents for safer chemical synthesis.

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Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase
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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Catalysis

Background:

  • Amides are generally unreactive carbonyl compounds due to low electrophilicity and high stability.
  • Selective amide reduction is crucial for synthesizing valuable chemical building blocks.
  • Existing reduction methods often involve hazardous reagents or harsh conditions.

Purpose of the Study:

  • To develop an efficient and selective electroreduction method for amides to amines.
  • To establish a safer alternative to traditional amide reduction techniques.
  • To explore the synthesis of functionalized and diverse amines using electrochemistry.

Main Methods:

  • Electrochemical reduction of amides using protons as the hydrogen source.
  • Utilized a zirconium catalyst (Cp2ZrCl2) in combination with a stoichiometric halosilane.
  • Investigated the reaction mechanism, identifying an α-aminocarbene intermediate.

Main Results:

  • Achieved selective deoxygenative electroreduction of amides to amines under mild conditions.
  • Demonstrated the synthesis of various functionalized and structurally diverse amines.
  • Successfully synthesized N-α-deuterated amines using deuterium sources.

Conclusions:

  • The developed electrochemical protocol offers an efficient, selective, and safe method for amide reduction.
  • This approach avoids the need for flammable H2 gas or sensitive hydrides.
  • The protocol provides practical access to diverse amines and deuterated amines.