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

6.3K
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.
6.3K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

8.0K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
8.0K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

18.7K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
18.7K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.6K
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...
3.6K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.4K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.4K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

4.0K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
4.0K

You might also read

Related Articles

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

Sort by
Same author

Ultrasonic and mechanochemical strategies for the synthesis of oxindole scaffolds mediated by hypervalent iodine(iii) reagents.

RSC advances·2026
Same author

Hydrogen bonding interactions in HFIP enabling the cascade synthesis of sulfenylated 2<i>H</i>-chromenes.

Chemical communications (Cambridge, England)·2026
Same author

Borane catalysed annulative sulfenylation of internal alkynes: towards the synthesis and study of fused heterocycles.

Chemical science·2026
Same author

Iron-Catalyzed Nucleophilic Substitution Reactions: An Overview.

ACS omega·2026
Same author

Synthesis and Structure of Group 13 POCOP Complexes.

Inorganic chemistry·2026
Same author

Revealing the Mechanism of TEMPO-Hypervalent Iodine(III) Oxidation of Alcohols.

Journal of the American Chemical Society·2026

Related Experiment Video

Updated: Aug 29, 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

7.8K

Progress in organocatalysis with hypervalent iodine catalysts.

Fateh V Singh1, Samata E Shetgaonkar1, Manjula Krishnan1

  • 1Chemistry Department, SAS, Vellore Institute of Technology - Chennai, Vandalur-Kelambakkam Road, Chennai-600127, Tamil Nadu, India. fatehveer.singh@vit.ac.in.

Chemical Society Reviews
|September 5, 2022
PubMed
Summary

Hypervalent iodine compounds offer a green and cost-effective alternative to transition metals in organic synthesis. These catalysts facilitate diverse bond formations and enable stereoselective synthesis, with supported catalysts also discussed.

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

10.9K
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

10.1K

Related Experiment Videos

Last Updated: Aug 29, 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

7.8K
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

10.9K
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

10.1K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Hypervalent iodine compounds are emerging as sustainable alternatives to transition metal catalysts.
  • They offer mild, non-toxic, selective, and recyclable catalytic properties.
  • Their utility spans various bond formations, including C-N, C-O, C-S, C-F, and C-C.

Purpose of the Study:

  • To review recent advancements in using iodine(III) and iodine(V) catalysts.
  • To highlight their application in synthesizing diverse organic compounds.
  • To showcase chiral catalysts for stereoselective synthesis and supported hypervalent iodine catalysts.

Main Methods:

  • Review of literature on hypervalent iodine-catalyzed reactions.
  • Focus on oxidative functionalization reactions.
  • Discussion of supported hypervalent iodine catalysts (polymer-, nanoparticle-, MOF-supported).

Main Results:

  • Hypervalent iodine catalysts efficiently promote the formation of C-N, C-O, C-S, C-F, and C-C bonds.
  • These catalysts are effective in stereoselective synthesis, including the use of chiral variants.
  • Development of supported hypervalent iodine catalysts for enhanced recyclability and application.

Conclusions:

  • Hypervalent iodine chemistry provides a powerful and environmentally benign platform for organic synthesis.
  • The versatility extends to stereoselective transformations and heterogeneous catalysis.
  • These reagents represent a significant advancement in sustainable catalytic methods.