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

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

5.8K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
5.8K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.1K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
8.1K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.8K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.8K
Halogenation of Alkenes02:46

Halogenation of Alkenes

15.2K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
15.2K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

15.6K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
15.6K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.4K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.4K

You might also read

Related Articles

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

Sort by
Same author

Ni(DQ)<sub>2</sub>: A Useful Gateway to Zero-Valent Nickel Complexes.

Organometallics·2026
Same author

Site-Divergent Oxidations within Venerable Macrolide Antibiotic Scaffolds Unveil Compounds with Broad Spectrum and Anti-MRSA Activities.

ACS central science·2026
Same author

Desymmetrization of <i>meso</i>-Pyrrolidines via Oxoammonium-Catalyzed Enantioselective Hydride Transfer.

Journal of the American Chemical Society·2026
Same author

Electrochemical Activation of α-Carbonyl Alkoxyamines for Direct Nucleophilic Substitution.

Organic letters·2026
Same author

Regioselective Electrochemical Borylation of Oxygenated Allylic Electrophiles: Method Development and Synthetic Applications.

ACS central science·2025
Same author

Experimental Lineage and Computational Analysis of a General Aminoxyl-Based Oxidation Catalyst: Generality from Substrate-Specific Interactions.

ACS catalysis·2025

Related Experiment Video

Updated: May 26, 2025

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
09:54

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

7.6K

Light-activated hypervalent iodine agents enable diverse aliphatic C-H functionalization.

Zhipeng Lu1, John Putziger1, Song Lin2

  • 1Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY, USA.

Nature Chemistry
|February 24, 2025
PubMed
Summary

This study introduces a novel hypervalent iodine reagent for mild, photochemically driven C-H activation. The method enables selective thiolation of aliphatic C-H bonds, offering versatile pathways for complex molecule synthesis.

More Related Videos

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

10.8K
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

13.8K

Related Experiment Videos

Last Updated: May 26, 2025

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
09:54

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

7.6K
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

10.8K
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

13.8K

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Photochemistry

Background:

  • Aliphatic C-H bond functionalization is vital for synthesizing complex molecules in medicinal, agricultural, and materials chemistry.
  • Developing efficient and general synthetic platforms for C-H bond diversification remains a significant challenge.

Purpose of the Study:

  • To develop a novel hypervalent iodine reagent for mild photochemical C-H activation.
  • To demonstrate selective thiolation of aliphatic C-H bonds using this reagent.
  • To showcase the broad synthetic utility of the thiolated products through various derivatizations.

Main Methods:

  • Utilized a hypervalent iodine reagent that generates a hydrogen atom abstractor under mild photochemical conditions.
  • Applied the reagent for selective (N-phenyltetrazole)thiolation of a wide range of aliphatic C-H bonds.
  • Explored derivatization of the thiolated products to access diverse functionalities.

Main Results:

  • Achieved selective thiolation of aliphatic C-H bonds across a broad substrate scope.
  • Demonstrated the synthetic versatility of the thiolated intermediates.
  • Showcased direct transformation of C-H bonds into C-S, C-Cl, C-Br, C-I, C-O, C-N, C-C, and C=C bonds by varying radical trapping agents.

Conclusions:

  • The developed hypervalent iodine reagent provides an efficient platform for aliphatic C-H bond functionalization under mild photochemical conditions.
  • The method offers a versatile approach to introduce diverse functionalities, significantly impacting synthetic chemistry.
  • This strategy broadens the scope of C-H activation methodologies for complex molecule synthesis.