Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.9K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.9K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.6K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.6K
Amides to Amines: LiAlH4 Reduction01:20

Amides to Amines: LiAlH4 Reduction

6.1K
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.
6.1K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.5K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
4.5K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.6K
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.
3.6K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

2.9K
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,...
2.9K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Unforgeable Red: Design and Application of SO-Annulated Perylene Diimides for Anti-Counterfeiting.

Small (Weinheim an der Bergstrasse, Germany)·2026
Same author

Gold(III) Semiquinone Complexes: Synthesis, Structure, and Application in Photocatalysis.

Angewandte Chemie (International ed. in English)·2026
Same author

Detection of antibodies to avian influenza virus H5N1 clade 2.3.4.4b in naturally infected cattle for more than a year.

Scientific reports·2026
Same author

Detection and Genomic Characterization of Novel Respiratory Viruses in US and Mexican Cattle Farms.

Transboundary and emerging diseases·2026
Same author

Visible-Light Unlocked Carbene Insertion and Radical Release in a Structurally Constrained Pincer Phosphorus Compound.

Angewandte Chemie (International ed. in English)·2026
Same author

Comparative efficacy of six monthly doses of Simparica Trio<sup>®</sup> (sarolaner, moxidectin, and pyrantel chewable tablets) versus NexGard<sup>®</sup> Plus (afoxolaner, moxidectin, and pyrantel chewable tablets) against a macrocyclic lactone-resistant Dirofilaria immitis isolate in dogs.

Parasites & vectors·2026

Related Experiment Video

Updated: Jan 2, 2026

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
07:20

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Published on: May 28, 2014

14.4K

Au(i)/Au(iii)-Catalyzed C-N coupling.

Jessica Rodriguez1, Nicolas Adet, Nathalie Saffon-Merceron

  • 1CNRS/Université Paul Sabatier, Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA, UMR 5069), 118 Route de Narbonne, 31062 Toulouse Cedex 09, France. dbouriss@chimie.ups-tlse.fr.

Chemical Communications (Cambridge, England)
|December 3, 2019
PubMed
Summary
This summary is machine-generated.

Gold catalysts enable efficient C-N cross-coupling of aryl iodides and amines. This novel gold(I)/gold(III) redox cycle operates under mild conditions without external oxidants, expanding synthetic possibilities.

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.3K
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

11.2K

Related Experiment Videos

Last Updated: Jan 2, 2026

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents
07:20

Amide Coupling Reaction for the Synthesis of Bispyridine-based Ligands and Their Complexation to Platinum as Dinuclear Anticancer Agents

Published on: May 28, 2014

14.4K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.3K
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

11.2K

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Organic Chemistry

Background:

  • Gold catalysis is limited by challenges in cycling between Au(I) and Au(III) oxidation states.
  • Gold-catalyzed cross-coupling reactions remain relatively rare in synthetic chemistry.

Purpose of the Study:

  • To develop an efficient gold-catalyzed method for C-N cross-coupling.
  • To investigate the mechanism of gold-catalyzed C-N bond formation.

Main Methods:

  • Utilized the (MeDalphos)AuCl complex for catalysis.
  • Employed aryl iodides and various N-nucleophiles.
  • Conducted mechanistic studies including NMR and MS characterization.

Main Results:

  • Achieved efficient C-N coupling of aryl iodides and amines using (MeDalphos)AuCl.
  • Demonstrated the reaction proceeds without external oxidants or directing groups.
  • Identified a key aryl amido Au(III) intermediate, supporting a 2e redox cycle.

Conclusions:

  • The (MeDalphos)AuCl complex effectively catalyzes C-N cross-coupling under mild conditions.
  • The reaction proceeds via a novel Au(I)/Au(III) redox pathway.
  • This method offers a robust and versatile approach for synthesizing C-N coupled products.