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

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.8K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.8K
Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

6.4K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
6.4K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.8K
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.
10.8K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.2K
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.
4.2K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.9K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.9K
Diels–Alder Reaction: Characteristics of Dienes01:29

Diels–Alder Reaction: Characteristics of Dienes

4.5K
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...
4.5K

You might also read

Related Articles

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

Sort by
Same author

Diazo-Preserving Radical Cascades for the Modular Photoinduced Synthesis of Oxindoles and Pyrazolones.

Organic letters·2026
Same author

Site-Selective Peptide and Protein Functionalization with Cyclopropenium Cations.

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

Catalytic Oxidative Ligand Transfer of Rh-Carbynoids and Alkyl Iodides.

Journal of the American Chemical Society·2025
Same author

Rh-Catalyzed Atroposelective Single-Carbon Insertion.

Journal of the American Chemical Society·2025
Same author

Rh-Catalyzed Enantioselective Aryl C-H Bond Cyclopropylation.

Journal of the American Chemical Society·2025
Same author

Late-Stage Photoredox-Catalyzed Aryl C-H Bond Diazomethylation with Atomic Carbon Reagents.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Sep 18, 2025

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

7.5K

Rh-catalysed single-carbon insertion to 1,3-dienes.

Pau Sarró1,2, Norman Díaz1,2, Josep Esteve Guasch1,2

  • 1Institute of Chemical Research of Catalonia (ICIQ-CERCA), The Barcelona Institute of Science and Technology Av. Països Catalans 16 43007 Tarragona Spain mgsuero@iciq.es.

Chemical Science
|June 23, 2025
PubMed
Summary

This study introduces a novel catalytic method for single-carbon insertion into 1,3-dienes using Rh(ii)-carbynoids. This skeletal editing reaction creates substituted dienes via a pentadienyl cation intermediate.

More Related Videos

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

9.9K
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

11.0K

Related Experiment Videos

Last Updated: Sep 18, 2025

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

7.5K
Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
10:42

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

Published on: January 3, 2018

9.9K
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

11.0K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • 1,3-Dienes are versatile building blocks in organic synthesis.
  • Catalytic methods for functionalizing dienes are crucial for creating complex molecules.
  • Direct carbon insertion into C-C bonds remains a synthetic challenge.

Purpose of the Study:

  • To develop a novel catalytic method for single-carbon insertion into 1,3-dienes.
  • To explore the reactivity of Rh(ii)-carbynoids in skeletal editing reactions.
  • To synthesize multi-substituted 1,3-dienes and 1,4-dienes.

Main Methods:

  • Catalytic generation of Rh(ii)-carbynoids.
  • Insertion of a cationic monovalent carbon unit into the C(sp2)-C(sp2) bond of 1,3-dienes.
  • Regioselective nucleophilic attack on the resulting pentadienyl cation.

Main Results:

  • First report of catalytic single-carbon insertion into 1,3-dienes using Rh(ii)-carbynoids.
  • Formation of a pentadienyl cation intermediate.
  • Synthesis of multi-substituted 1,3-dienes and 1,4-dienes using various nucleophiles.

Conclusions:

  • The developed method provides a new route for skeletal editing of 1,3-dienes.
  • This catalytic approach enables the efficient synthesis of diverse substituted dienes.
  • The methodology holds potential for constructing complex organic architectures.