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

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
[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.

You might also read

Related Articles

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

Sort by
Same author

A predictive corticospinal model for pain perception.

Cell reports. Medicine·2026
Same author

Visible-Light Photocatalytic and Phosphine-Mediated <i>In Situ</i> Wittig Reaction of Bicyclo[1.1.0]butanes with Aryl Aldehydes.

Organic letters·2026
Same author

C(<i>sp</i><sup>3</sup>)-H Activation/Cleavage of Alcohols and C-C Coupling with Nonactivated Alkenes through Rhodium Catalysis Triggered by O<sub>2</sub>.

Organic letters·2026
Same author

Amide-Based Polyene Cyclization: Stereoselective Construction of <i>cis</i>- or <i>trans</i>-Octahydrobenzo[<i>f</i>]isoquinolines.

Organic letters·2026
Same author

Benzo-Fused Medium-Sized Heterocycles with a Chiral C-N Axis from Asymmetric Cycloaddition and Skeletal Rearrangement.

Journal of the American Chemical Society·2026
Same author

UFMylation-dependent inhibition of AKT signaling by PHLDA3 in lung adenocarcinoma.

Cell reports·2026

Related Experiment Video

Updated: May 23, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Palladium-catalyzed cascade process to construct 1,2,5-trisubstituted pyrroles.

Yong-Qiang Zhang1, Dao-Yong Zhu, Bao-Sheng Li

  • 1State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, PR China.

The Journal of Organic Chemistry
|April 5, 2012
PubMed
Summary

A new palladium-catalyzed reaction creates 1,2,5-trisubstituted pyrroles from protected enynols and primary amines. This efficient method provides a straightforward synthetic route to valuable substituted pyrrole compounds.

More Related Videos

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Related Experiment Videos

Last Updated: May 23, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
10:17

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
19:58

Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions

Published on: July 30, 2017

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Pyrroles are essential heterocyclic compounds found in numerous natural products and pharmaceuticals.
  • Developing efficient and versatile synthetic routes to substituted pyrroles remains a key challenge in organic synthesis.

Purpose of the Study:

  • To explore a novel palladium-catalyzed cascade reaction for the synthesis of 1,2,5-trisubstituted pyrroles.
  • To establish a new synthetic methodology for constructing substituted pyrroles.

Main Methods:

  • A one-pot, three-step cascade process involving allylic amination, intramolecular hydroamination, and isomerization.
  • Utilized protected enynol and a primary amine as starting materials.
  • Employed a palladium catalyst to facilitate the transformation.

Main Results:

  • Successfully synthesized 1,2,5-trisubstituted pyrroles with high efficiency.
  • The reaction proceeds through a novel cascade sequence.
  • Demonstrated a straightforward and alternative method for pyrrole synthesis.

Conclusions:

  • The developed palladium-catalyzed cascade reaction is an effective method for synthesizing 1,2,5-trisubstituted pyrroles.
  • This transformation offers a valuable addition to the synthetic chemist's toolkit for accessing substituted pyrroles.