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

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the double...
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.

You might also read

Related Articles

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

Sort by
Same author

Scope and Limitations of the PdCl<sub>2</sub>(MeCN)<sub>2</sub>/Fe(OTf)<sub>3</sub>-Cocatalyzed Aerobic Olefin Aminoboration.

The Journal of organic chemistry·2026
Same author

Pd- and Cu-Cocatalyzed Anaerobic Olefin Aminoboration.

The Journal of organic chemistry·2025
Same author

Direct C─H Lactonization of Carboxylic Acids Enabled by LMCT Photoactivation.

Angewandte Chemie (International ed. in English)·2025
Same author

Chemoselective Cu-Catalyzed Cross-Nucleophile Alkylarylation of Alkenes.

ACS catalysis·2025
Same author

Palladium-Catalyzed Aerobic Alkene Arylboration: Coupling Aryl Boronic Acids, Alkenes, and Bis(pinacol)diboron.

ACS catalysis·2025
Same author

Reniochalistatin E: A potentiating agent and a potential novel drug delivery platform.

Bioorganic chemistry·2025

Related Experiment Video

Updated: Jul 16, 2026

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

Cu-Catalyzed Three-Component Carbofunctionalization of 1,3-Dienes.

Vincent R Viviani1, Travis L Buchanan1, An Thien Ho1

  • 1Department of Chemistry, University of Texas at Austin, Austin, Texas 78712, United States.

ACS Catalysis
|July 15, 2026
PubMed
Summary

This study introduces a novel three-component carboamination reaction for synthesizing allylic amines from 1,3-dienes. The atom transfer radical addition (ATRA) method offers a versatile and efficient route to diverse amine structures.

Keywords:
Carbofunctionalizationatom transfer radical additionconjugated dienescopper catalysismulticomponent functionalization

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

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Related Experiment Videos

Last Updated: Jul 16, 2026

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

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

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
10:12

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Allylic amines are crucial building blocks in pharmaceuticals and natural products.
  • Existing methods for allylic amine synthesis often lack efficiency or modularity.

Purpose of the Study:

  • To develop a novel three-component carboamination reaction for efficient allylic amine synthesis.
  • To demonstrate the modularity and broad scope of the developed reaction.

Main Methods:

  • A three-component reaction involving 1,3-dienes, activated alkyl halides, and amines.
  • Mechanistic studies utilizing atom transfer radical addition (ATRA).
  • Expansion to a two-step, one-pot carbofunctionalization process.

Main Results:

  • Achieved high yields (up to 96%) for a diverse range of allylic amines.
  • Demonstrated high regioisomeric ratios (≥12:1) for both 1,2- and 1,4-carboamination.
  • Successfully expanded the reaction to include various nucleophiles (O, S, P, C) for general carbofunctionalization.

Conclusions:

  • The developed three-component carboamination reaction provides a modular and efficient pathway to allylic amines.
  • The reaction proceeds via an ATRA mechanism, generating an isolable allylic halide intermediate.
  • The methodology is versatile, enabling further carbofunctionalization in a one-pot process.