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 Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

3.9K
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,...
3.9K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

3.7K
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...
3.7K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.0K
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.
3.0K
Preparation of Amines: Reduction of Amides and Nitriles01:13

Preparation of Amines: Reduction of Amides and Nitriles

2.6K
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,...
2.6K
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview01:26

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview

3.4K
Nitrous acid and nitric acids are two types of acids containing nitrogen, among which nitrous acid is weaker than nitric acid. Nitrous acid with a pKa value of 3.37 ionizes in water to give a nitrite ion and the hydronium ion.
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
3.4K
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

4.9K
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.
4.9K

You might also read

Related Articles

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

Sort by
Same author

Direct Deaminative C(sp<sup>3</sup>)-N Cross-Coupling via Copper Catalysis.

Organic letters·2026
Same author

Long-term survival after multimodal therapy for advanced hepatocellular carcinoma: a case report.

Frontiers in immunology·2026
Same author

Multicenter comparison of three automated procalcitonin (PCT) assays and commutability evaluation of EQA/PT materials.

Clinica chimica acta; international journal of clinical chemistry·2026
Same author

Influencing factors for rapidly progressive interstitial lung disease in patients with anti-MDA5 antibody-positive dermatomyositis: a systematic review and meta-analysis.

Frontiers in immunology·2026
Same author

NaO<sub>6</sub> Octahedron-Engineered Sodium Iron Sulfate Cathodes for High-Rate and Sustainable Sodium-Ion Batteries.

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

Microglial PD-1/PD-L1 axis in CNS demyelinating diseases: a dual immunoregulatory perspective.

Frontiers in cellular neuroscience·2026

Related Experiment Video

Updated: Aug 13, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

10.4K

Nitrene transfer reaction with hydroxylamine derivatives.

Yang Gao1,2, Haixia Li1, Yupeng Zhao1

  • 1School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou, 510006, China.

Chemical Communications (Cambridge, England)
|January 20, 2023
PubMed
Summary

Hydroxylamine derivatives enable efficient nitrene transfer reactions, facilitating new C-H amination and N-X bond formations. These versatile reagents are activated by transition metals, photocatalysis, and enzymes for broad synthetic applications.

More Related Videos

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.2K
Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

8.5K

Related Experiment Videos

Last Updated: Aug 13, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

10.4K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.2K
Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
06:18

Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

Published on: April 24, 2018

8.5K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Nitrene transfer reactions are crucial for forming nitrogen-containing compounds.
  • Hydroxylamine derivatives offer a stable and accessible source of nitrene precursors.

Purpose of the Study:

  • To summarize recent advancements in catalytic nitrene transfer reactions using hydroxylamine derivatives.
  • To highlight the versatility and applications of these reagents in modern organic synthesis.

Main Methods:

  • Activation of hydroxylamine derivatives using various transition metal catalysts.
  • Application in diverse reactions including C-H amination, aziridination, and difunctionalization.
  • Exploration of photocatalysis and enzyme catalysis for nitrene transfer.

Main Results:

  • Development of novel amidation and amination reactions.
  • Successful C-H insertion and olefin aziridination.
  • Application in dearomative amination of indoles and N-X bond formation.
  • Demonstrated utility in photocatalytic and enzymatic systems.

Conclusions:

  • Hydroxylamine derivatives are valuable, bench-stable nitrene transfer reagents.
  • These reagents enable a wide array of transformations under mild conditions.
  • Future opportunities lie in expanding catalytic systems and reaction scope.