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

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.4K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.4K
Radical Formation: Addition00:47

Radical Formation: Addition

2.0K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
2.0K
Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

4.2K
Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
4.2K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.4K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.4K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.2K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
2.2K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.0K
Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
2.0K

You might also read

Related Articles

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

Sort by
Same author

RIMTAC: A Novel Degrader Design Platform by Indirect VHL-Recruitment via RIPK1.

Journal of medicinal chemistry·2026
Same author

AAV8-Mediated Retinal PD-L1 Gene Transfer Attenuates Experimental Autoimmune Uveitis by Restoring Local Immune Tolerance.

Investigative ophthalmology & visual science·2026
Same author

Unique Cysteine-Directed Covalent Inhibition of PRMT1 Suppresses Breast Tumorigenesis.

Journal of medicinal chemistry·2026
Same author

OsPHR2-OsDIR55 Module Enhances Root Barrier Integrity and Rice Tolerance to Phosphate Deficiency.

Plant, cell & environment·2026
Same author

Robot-assisted tracheal carina resection and reconstruction for adenoid cystic carcinoma: a case report.

Journal of cardiothoracic surgery·2026
Same author

Exploring mitochondrial genetic features in intervertebral disc degeneration through multi-omics integration analyses.

The journals of gerontology. Series A, Biological sciences and medical sciences·2026

Related Experiment Video

Updated: Nov 17, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.6K

Three-component radical homo Mannich reaction.

Shuai Shi1, Wenting Qiu1, Pannan Miao1

  • 1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Pharmacy, Shanghai Jiao Tong University, No. 800 Dongchuan Rd., 200240, Shanghai, China.

Nature Communications
|February 13, 2021
PubMed
Summary
This summary is machine-generated.

This study introduces a novel radical homo Mannich reaction, enabling the synthesis of complex gamma-amino-carbonyl compounds using enolizable aldehydes. This metal-free method offers a streamlined approach for creating valuable tertiary amine scaffolds.

More Related Videos

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.3K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.7K

Related Experiment Videos

Last Updated: Nov 17, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.6K
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

11.3K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

25.7K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Tertiary aliphatic amines are crucial functionalities in pharmaceutical agents.
  • The classical Mannich reaction synthesizes beta-amino-carbonyl compounds but is limited to non-enolizable aldehydes.
  • This limitation restricts the synthetic utility of the Mannich reaction.

Purpose of the Study:

  • To develop a novel synthetic strategy for gamma-amino-carbonyl compounds.
  • To overcome the substrate limitations of the traditional Mannich reaction.
  • To establish a streamlined, metal-free method for synthesizing complex tertiary amine scaffolds.

Main Methods:

  • A three-component radical homo Mannich reaction was developed.
  • Electrophilic radicals were generated from thiols via visible-light-mediated desulfurization.
  • In-situ formed enamines reacted with these radicals to yield products in a single step.

Main Results:

  • The reaction successfully utilized enolizable aldehydes, expanding substrate scope.
  • Gamma-amino-carbonyl compounds were synthesized efficiently.
  • The process demonstrated broad scope, mild conditions, and high functional group tolerance.

Conclusions:

  • A novel, metal-free radical homo Mannich reaction was established.
  • This method provides a streamlined synthesis of gamma-amino-carbonyl compounds.
  • The approach offers significant utility for synthesizing complex tertiary amine scaffolds in academia and industry.