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

Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.4K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.4K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.2K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.2K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

11.2K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
11.2K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.9K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene

8.5K
The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
8.5K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

10.1K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.1K

You might also read

Related Articles

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

Sort by
Same author

Influencing factors of functional exercise adherence in stroke survivors: a cross-sectional study based on structural equation modeling.

Scientific reports·2026
Same author

Synthesis of 9-(Piperidin-3-yl)purine Derivatives <i>via</i> [4 + 2] Cycloaddition of Aza-π-allylpalladium 1,4-Dipole.

Organic letters·2026
Same author

Photoelectrocatalysis-Enabled C(sp<sup>3</sup>)-C(sp<sup>3</sup>) Cross-Coupling of Carboxylic Acids with Alkyl Halides.

Journal of the American Chemical Society·2026
Same author

MCF-YOLO: Consistency-Guided Cross-Modal Attention for Small-Object RGB-IR Detection.

Sensors (Basel, Switzerland)·2026
Same author

Catalytic Asymmetric Nucleophilic Amination and Kinetic Resolution of α-Bromo-acylpyrazoles.

Organic letters·2026
Same author

Salicylaldehyde-functionalized gold-nanocluster-based Ratiometric fluorescent sensor Array for metal-ion detection.

Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy·2026

Related Experiment Video

Updated: Jan 4, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

14.3K

Electrochemistry-Enabled Ir-Catalyzed Vinylic C-H Functionalization.

Qi-Liang Yang1,2, Yi-Kang Xing1, Xiang-Yang Wang1

  • 1State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , China.

Journal of the American Chemical Society
|November 13, 2019
PubMed
Summary

This study introduces electrochemical vinylic C-H functionalization using iridium catalysis for alkyne annulation. The method efficiently produces valuable α-pyrones from acrylic acids and alkynes.

More Related Videos

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
Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
09:17

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

Published on: January 30, 2015

12.3K

Related Experiment Videos

Last Updated: Jan 4, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

14.3K
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
Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes
09:17

Reductive Electropolymerization of a Vinyl-containing Poly-pyridyl Complex on Glassy Carbon and Fluorine-doped Tin Oxide Electrodes

Published on: January 30, 2015

12.3K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Electrochemistry

Background:

  • Site-selective C-H functionalization is crucial in organic synthesis.
  • Organometallic catalysis and electrochemistry offer powerful synergistic approaches.
  • Current methods predominantly focus on arene C-H functionalization.

Purpose of the Study:

  • To develop a novel electrochemical method for vinylic C-H functionalization.
  • To achieve site-selective annulation of acrylic acids with alkynes.
  • To synthesize α-pyrones using a combination of electrochemistry and iridium catalysis.

Main Methods:

  • Electrochemical oxidation in an undivided cell.
  • Utilizing an iridium catalyst for C-H/O-H functionalization.
  • Reaction of acrylic acids with alkynes.

Main Results:

  • Efficient synthesis of α-pyrones with good to excellent yields.
  • Demonstration of electrochemical vinylic C-H functionalization, expanding beyond arenes.
  • Anodic oxidation identified as critical for product release and catalyst regeneration.
  • Comparison with chemical oxidants showing the necessity of electrical current.

Conclusions:

  • Electrochemical vinylic C-H functionalization is a viable and efficient synthetic strategy.
  • The developed method provides a novel route to α-pyrones.
  • The synergistic electro-organometallic approach overcomes limitations of previous methods.