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

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.0K
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...
4.0K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

15.0K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
15.0K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.5K
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.
9.5K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

8.1K
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.
8.1K
Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

2.8K
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 of a...
2.8K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

13.6K
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.
13.6K

You might also read

Related Articles

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

Sort by
Same author

Making a Health System Merger Succeed: Michigan Medicine's Journey Toward a High-Quality, Coordinated Statewide System of Care.

NEJM catalyst innovations in care delivery·2026
Same author

Enantioselective Contrathermodynamic Olefin Isomerization.

Journal of the American Chemical Society·2026
Same author

Leveraging Multiproton-Coupled Electron Transfer to Improve Ir(III) Photocatalyst Efficiency.

The journal of physical chemistry. C, Nanomaterials and interfaces·2026
Same author

Asymmetric Hydrogen Atom Transfer.

ACS catalysis·2026
Same author

Correction to "[2 + 2] Photocycloadditions of Conformationally Constrained Styrenes Enabled by Triplet Lifetime Extension".

The Journal of organic chemistry·2025
Same author

Light-Driven Crystallization-Induced Dynamic Resolution of Amines.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Apr 1, 2026

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

4.2K

Catalytic Olefin Hydroamidation Enabled by Proton-Coupled Electron Transfer.

David C Miller1, Gilbert J Choi1, Hudson S Orbe1

  • 1Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.

Journal of the American Chemical Society
|October 7, 2015
PubMed
Summary

Researchers developed a new catalytic system for intramolecular hydroamidation using iridium photocatalysis. This method efficiently creates amidyl radicals from amides via concerted proton-coupled electron transfer (PCET) for alkene functionalization.

More Related Videos

Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

12.4K
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

8.7K

Related Experiment Videos

Last Updated: Apr 1, 2026

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

4.2K
Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

12.4K
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

8.7K

Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Catalysis

Background:

  • Intramolecular hydroamidation is a valuable synthetic transformation.
  • Activation of unactivated olefins and simple amide derivatives remains challenging.
  • Developing efficient catalytic systems for these reactions is crucial.

Purpose of the Study:

  • To report a novel ternary catalyst system for the intramolecular hydroamidation of unactivated olefins.
  • To utilize simple N-aryl amide derivatives as substrates.
  • To elucidate the mechanism of amide activation and radical generation.

Main Methods:

  • Employing an excited state iridium complex as a photocatalyst.
  • Utilizing a weak phosphate base to mediate concerted proton-coupled electron transfer (PCET).
  • Incorporating a thiophenol cocatalyst to facilitate radical transfer and catalyst regeneration.

Main Results:

  • The system successfully achieves intramolecular hydroamidation of unactivated olefins.
  • Amide activation occurs via PCET, generating a reactive amidyl radical.
  • Mechanistic studies confirm selective amide homolysis by PCET, even with a thiophenol present.

Conclusions:

  • The developed ternary catalyst system enables efficient intramolecular hydroamidation.
  • PCET is a key mechanism for activating amides and generating amidyl radicals.
  • The system demonstrates selectivity and robustness in the presence of a thiophenol cocatalyst.