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

Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.8K
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
1.8K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.3K
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.
2.3K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.1K
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.
2.1K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.6K
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.
2.6K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.2K
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.
10.2K
Diels–Alder Reaction: Characteristics of Dienophiles01:24

Diels–Alder Reaction: Characteristics of Dienophiles

6.1K
In a Diels–Alder reaction, the diene is usually an electron-rich system and acts as a nucleophile, whereas the dienophile is electron-deficient and functions as an electrophile. Much like the diene, the nature of the dienophile significantly impacts the outcome of the reaction. 
Characteristics of Dienophiles
Generally, the best dienophiles are alkenes containing electron-withdrawing substituents such as carbonyl, nitrile, and nitro groups. The feasibility of a Diels–Alder reaction depends...
6.1K

You might also read

Related Articles

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

Sort by
Same author

Sediment heterogeneity shapes benthic microbial community assembly and co-occurrence network organization in the East China Sea.

Marine environmental research·2026
Same author

Transcriptomic analysis of response to high-temperature stress in cotton.

Plant physiology and biochemistry : PPB·2026
Same author

Metabolic engineering of Halomonas cupida for co-mineralization of phenol and p-nitrophenol in high-saline wastewater.

Journal of environmental management·2026
Same author

Quantitative prediction and degradation mechanism of CFRP-TC4 adhesive joints under hygrothermal aging.

Scientific reports·2026
Same author

Prefrontal dysregulation of interoceptive and emotional processing in episodic migraine: a task-based fMRI study.

The journal of headache and pain·2026
Same author

Photoinduced Fluoroalkylalkynylation of Unactivated Alkenes with Terminal Alkynes.

Organic letters·2026

Related Experiment Video

Updated: Jul 9, 2025

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

13.9K

Photo-induced versatile aliphatic C-H functionalization via electron donor-acceptor complex.

Zemin Wang1, Chao-Xian Yan2, Ruihua Liu1

  • 1State Key Laboratory of Microbial Technology, Shandong University, Qingdao 266237, China.

Science Bulletin
|December 3, 2023
PubMed
Summary

This study introduces a novel, metal-free method for functionalizing hydrocarbons using an electron donor-acceptor (EDA) strategy. This approach enables versatile aliphatic C-H bond diversification under mild conditions.

Keywords:
Aliphatic C–H functionalizationChlorine radicalsElectron donor–acceptorGaseous alkanesPhotoreaction

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.0K
Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

8.5K

Related Experiment Videos

Last Updated: Jul 9, 2025

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

13.9K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.0K
Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
12:19

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Published on: November 29, 2018

8.5K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Sustainable Chemistry

Background:

  • Selective functionalization of hydrocarbons is crucial for synthesizing small molecules and pharmaceuticals.
  • Electron donor-acceptor (EDA) strategies are underexplored for photocatalyst- and metal-free hydrocarbon functionalization.

Purpose of the Study:

  • To develop a novel photocatalyst- and metal-free method for aliphatic C-H bond diversification.
  • To explore the utility of an EDA complex involving HCl and S(IV)=O groups for C-H functionalization.

Main Methods:

  • Utilized an electron donor-acceptor (EDA) complex of HCl and S(IV)=O groups.
  • Employed a proton-coupled electron transfer process to generate chlorine radicals.
  • Developed a photo-promoted C-H functionalization strategy without photo- or metal-catalysts.

Main Results:

  • Achieved versatile aliphatic C-H functionalization including thiolation, arylation, alkynylation, and allylation.
  • Demonstrated the generation of chlorine radicals via an unusual proton-coupled electron transfer pathway.
  • Showcased the process under concise and ambient reaction conditions with good functional group tolerance and substrate diversity.

Conclusions:

  • Developed an efficient, photocatalyst- and metal-free approach for aliphatic C-H bond diversification.
  • The EDA strategy offers a new pathway for utilizing bulk light alkanes.
  • This method provides a valuable alternative for synthesizing high value-added chemicals.