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: 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
ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

6.0K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
6.0K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
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
1.9K
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

1.2K
When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
1.2K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.5K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.5K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.8K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.8K

You might also read

Related Articles

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

Sort by
Same author

Visible-Light-Enabled Ir-Catalyzed Asymmetric Allylic Etherification and Dearomative Photocycloaddition.

Journal of the American Chemical Society·2026
Same author

Enantioselective Synthesis of Indole-Derived Atropisomers through Rh(I)-Catalyzed C-H Arylation with Aryl Bromides.

Organic letters·2026
Same author

Asymmetric Alkene Boration and <i>Z</i>-Retentive Allylic Substitution Reactions under Cu/Pd Relay Catalysis.

Journal of the American Chemical Society·2026
Same author

Visible-light-enabled excited-state dearomatization reactions.

Science advances·2026
Same author

Stereodivergent Access to Aliphatic Nitro Compounds Bearing Multi-Contiguous Stereocenters via Sequential Catalysis.

Advanced science (Weinheim, Baden-Wurttemberg, Germany)·2026
Same author

Rhodium-Catalyzed Enantioselective Synthesis of Planar-Chiral Macrocycles via De Novo Isoquinoline Formation.

Angewandte Chemie (International ed. in English)·2026
Same journal

Fluorescent merocyanines: from fundamental properties to applications as molecular probes, in bioimaging and as emissive dye aggregates.

Chemical Society reviews·2026
Same journal

Direct impure water electrolysis at industrial scale.

Chemical Society reviews·2026
Same journal

Catalytic valorization of polyolefins: from catalysts and processes to reactors.

Chemical Society reviews·2026
Same journal

Designing stable π-radicals.

Chemical Society reviews·2026
Same journal

Antibacterial drug discovery: challenges and preclinical promises from synthetic small molecules.

Chemical Society reviews·2026
Same journal

Selective carbon-carbon bond cleavage involving alkene moieties.

Chemical Society reviews·2026
See all related articles

Related Experiment Video

Updated: Oct 2, 2025

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

12.0K

Visible-light induced dearomatization reactions.

Yuan-Zheng Cheng1, Zuolijun Feng1, Xiao Zhang2

  • 1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, 345 Lingling Lu, Shanghai 200032, China. slyou@sioc.ac.cn.

Chemical Society Reviews
|February 25, 2022
PubMed
Summary
This summary is machine-generated.

Visible-light photocatalysis enables efficient dearomatization reactions, transforming simple aromatic compounds into complex 3D molecules. This review overviews these reactions, highlighting methods for disrupting aromaticity using light.

More Related Videos

Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

11.9K
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

17.3K

Related Experiment Videos

Last Updated: Oct 2, 2025

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

12.0K
Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

11.9K
Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
12:07

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

17.3K

Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Synthetic Chemistry

Background:

  • Dearomatization reactions offer efficient synthesis of complex 3D molecules from aromatic precursors.
  • These reactions are crucial in natural product synthesis, medicinal chemistry, and materials science.
  • Visible-light photocatalysis has become a powerful tool for various chemical transformations.

Purpose of the Study:

  • To provide a comprehensive overview of dearomatization reactions.
  • To focus specifically on reactions induced by visible-light photocatalysis.
  • To classify these reactions based on the mechanism of aromaticity disruption.

Main Methods:

  • Literature review of recent advances in visible-light induced dearomatization.
  • Classification of reactions based on the disruption of aromaticity.
  • Analysis of the scope and limitations of different photocatalytic dearomatization strategies.

Main Results:

  • Significant progress has been made in visible-light induced dearomatization reactions.
  • Various strategies exist for disrupting aromaticity using photocatalysis.
  • These methods provide rapid access to diverse and complex molecular architectures.

Conclusions:

  • Visible-light photocatalysis is a versatile and powerful approach for dearomatization.
  • Understanding the classification based on aromaticity disruption aids in reaction selection.
  • This field continues to expand, offering new synthetic possibilities.