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

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.6K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.6K
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

2.0K
Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
2.0K
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.2K
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...
2.2K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.2K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

6.0K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
6.0K
Sharpless Epoxidation02:57

Sharpless Epoxidation

4.1K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
4.1K

You might also read

Related Articles

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

Sort by
Same author

Multicomponent Hosomi-Sakurai Reaction on Isosorbide Derivatives.

Molecules (Basel, Switzerland)·2026
Same author

Solvent and Substitution Effects on the Excited-State Dynamics of Triphenylamines [6π] Electrocyclization: A Laser Flash Photolysis Investigation.

The Journal of organic chemistry·2026
Same author

Polydomain Liquid Crystal Elastomers with Mechanically Switchable Opacity for Thermal Shielding.

ACS polymers Au·2026
Same author

Selective functionalization of the 1,6-anhydro moiety and of the double bond of levoglucosenone.

Organic & biomolecular chemistry·2026
Same author

Synthesis of aryl sulfides <i>via</i> visible light-induced solventylation in diarylazo sulfides.

Chemical communications (Cambridge, England)·2026
Same author

Arylazo Sulfones as 1,3-Dipole Acceptors in the (Photo)-Micellar van Leusen Triazole Synthesis.

ACS organic & inorganic Au·2025

Related Experiment Video

Updated: Aug 15, 2025

Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

11.8K

Visible-Light-Driven Solventylation Strategy for Olefin Functionalization.

Pietro Capurro1, Valentina Ricciardiello1, Paola Lova1

  • 1Dipartimento di Chimica e Chimica Industriale, Università degli Studi di Genova, Via Dodecaneso 31, 16146 Genova, Italy.

ACS Omega
|January 2, 2023
PubMed
Summary
This summary is machine-generated.

Visible light generates amphiphilic aryl radicals from arylazo sulfones for versatile olefin functionalization. This metal- and photocatalyst-free method uses hydrogen atom transfer (HAT) for efficient carbon-centered radical addition.

More Related Videos

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

11.9K
Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

8.0K

Related Experiment Videos

Last Updated: Aug 15, 2025

Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

11.8K
Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
06:49

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

Published on: April 22, 2016

11.9K
Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

8.0K

Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Radical Chemistry

Background:

  • Visible light photoredox catalysis has enabled new synthetic transformations.
  • Arylazo sulfones are precursors to aryl radicals.
  • Hydrogen atom transfer (HAT) is a key radical reaction mechanism.

Purpose of the Study:

  • To develop a metal- and photocatalyst-free solventylation strategy for olefin functionalization.
  • To utilize amphiphilic aryl radicals generated from arylazo sulfones.
  • To achieve versatile functionalization of olefins with various carbon-centered radicals.

Main Methods:

  • Visible light irradiation of arylazo sulfones to generate aryl radicals.
  • Employing a hydrogen atom transfer (HAT) mechanism for radical addition.
  • Utilizing high dilution conditions to suppress direct aryl radical addition to olefins.

Main Results:

  • Successful functionalization of various olefins with carbon-centered radicals derived from acetone, acetonitrile, chloroform, methylene chloride, nitromethane, methyl acetate, and methyl formate.
  • Demonstration of a versatile solventylation strategy under metal- and photocatalyst-free conditions.
  • Suppression of undesired side reactions, such as direct addition of aryl radicals, via high dilution.

Conclusions:

  • A novel and versatile solventylation protocol for olefin functionalization has been established.
  • The method efficiently employs amphiphilic aryl radicals generated under visible light irradiation.
  • The developed strategy operates under mild, metal- and photocatalyst-free conditions, offering a sustainable approach.