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: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.7K
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.
3.7K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.6K
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...
4.6K
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
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.6K
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,...
4.6K
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
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.8K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.8K

You might also read

Related Articles

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

Sort by
Same author

Influence of the cation in hypophosphite-mediated catalyst-free reductive amination.

Beilstein journal of organic chemistry·2025
Same author

Cobalt-Catalyzed Green Alkylations of Anilines with Tetrahydrofurans.

ChemSusChem·2025
Same author

Reductive Amination Reactions Using Sodium Hypophosphite: a Guide to Substrates.

The Journal of organic chemistry·2025
Same author

Catalytic insertion of nitrenes into B-H bonds.

Chemical science·2025
Same author

Rhodotorula mucilaginosa: a new potential human pathogen found in the ciliate Paramecium bursaria.

Protoplasma·2025
Same author

Cyano-Fluorosulfonylation of Unactivated Alkenes by Photoredox and Copper Dual Catalysis.

Organic letters·2024
Same journal

A General Photocatalytic Decarboxylative Hydrogenation of Carboxylic Acids in Batch and Flow under Metal-Free Conditions.

Organic letters·2026
Same journal

Direct Access to Sulfonamidated-1,4-Benzoquinones via Sulfonamidation of Aryl Alcohol-Derived Quinone Monoacetals.

Organic letters·2026
Same journal

Photo/Cerium Co-Catalyzed Hydroalkylation of Alkynes Via Decarboxylative Ring-Opening of Cyclic Carboxylic Acids.

Organic letters·2026
Same journal

Electrochemical Dehydroxylative Thiolation of Alkyl Alcohols with Disulfides.

Organic letters·2026
Same journal

Molybdenum-Catalyzed Intramolecular Deoxygenative Annulation of 2-(Formamido)aryl Ketones to Access 3-Monosubstituted Oxindoles.

Organic letters·2026
Same journal

Modular Synthesis of Spiroisochromans with Spiro Quaternary Carbon Centers Via TBAT-Promoted Multicomponent Cascade Reactions.

Organic letters·2026
See all related articles

Related Experiment Video

Updated: Jan 9, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.6K

Sodium Hypophosphite Assisted Ruthenium Catalyzed Reductive Amination under Mild Conditions.

Olesya Zvereva1,2, Fedor S Kliuev1,2, Natalia Lebedeva1

  • 1A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, INEOS, Vavilova St. 28, Moscow 119334, Russia.

Organic Letters
|December 8, 2025
PubMed
Summary
This summary is machine-generated.

A new catalytic method for reductive amination uses inexpensive sodium hypophosphite. This environmentally friendly approach, employing CpRu(PPh3)2Cl, works under mild conditions and shows broad functional group tolerance.

More Related Videos

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
10:39

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

8.3K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

7.8K

Related Experiment Videos

Last Updated: Jan 9, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

12.6K
Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction
10:39

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

8.3K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

7.8K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Reductive amination is a key transformation in organic synthesis.
  • Developing efficient and sustainable methods is crucial for modern chemistry.
  • Existing methods often require harsh conditions or expensive reagents.

Purpose of the Study:

  • To develop a novel catalytic method for reductive amination.
  • To utilize a cost-effective and environmentally benign reducing agent.
  • To investigate the reaction mechanism and identify catalytic species.

Main Methods:

  • Catalytic reductive amination using CpRu(PPh3)2Cl.
  • Employing sodium hypophosphite as the reducing agent.
  • Mechanistic studies including NMR spectroscopy.

Main Results:

  • The reaction proceeded under mild conditions with high yields.
  • The method exhibited excellent functional group tolerance.
  • A Ru-hydride complex was identified as a potential catalytic intermediate.
  • A plausible reaction mechanism was proposed.

Conclusions:

  • A new, efficient, and green catalytic method for reductive amination has been established.
  • Sodium hypophosphite is a viable and sustainable reductant for this transformation.
  • The mechanistic insights provide a foundation for further optimization and development.