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

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

6.1K
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...
6.1K
Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
1.7K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.1K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.1K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
2.1K
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

3.9K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
3.9K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.2K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.2K

You might also read

Related Articles

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

Sort by
Same author

Dual Targeting of Nucleotidase-Dependent and -Independent Functions via PROTAC-Mediated CD73 Degradation.

Journal of medicinal chemistry·2026
Same author

Isolation and synthesis of bisabosquals, fungal triprenyl phenol meroterpenoids with a densely functionalised bisabolane core.

Natural product reports·2026
Same author

Enantioselective Total Synthesis of (-)-Bisabosqual F via N-Heterocyclic Carbene Catalyzed (4+2) Annulation.

Angewandte Chemie (International ed. in English)·2025
Same author

Phosphine-Mediated (3 + 2) Cycloaddition of Electron-Poor Terminal Alkynes: A Concise Route to Premethylenomycin C Lactone.

The Journal of organic chemistry·2025
Same author

Electroinduced Reductive and Dearomative Alkene-Aldehyde Coupling.

Journal of the American Chemical Society·2024
Same author

Enantioselective Synthesis of Cyclopentanes by Phosphine-Catalyzed β,γ-Annulation of Allenoates.

Organic letters·2024

Related Experiment Video

Updated: Jul 30, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.3K

Radical Coupling Initiated by Organophosphine Addition to Ynoates.

Jing Cao1, Antonia Seitz1, José A Forni2

  • 1School of Chemistry, Monash University, Clayton, 3800, Victoria, Australia.

Angewandte Chemie (International Ed. in English)
|May 15, 2023
PubMed
Summary

This study introduces a novel dual nucleophilic phosphine photoredox catalysis method for Giese coupling with ynoates. The innovative reaction design prevents catalyst oxidation, enabling efficient and general synthetic applications.

Keywords:
Dual CatalysisGiese ReactionMechanistic StudiesPhosphine OrganocatalysisPhotoredox Catalysis

More Related Videos

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.2K
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.3K

Related Experiment Videos

Last Updated: Jul 30, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
09:58

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts

Published on: February 24, 2015

11.3K
A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.2K
Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
07:50

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

Published on: May 26, 2019

9.3K

Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Catalysis

Background:

  • Dual nucleophilic phosphine photoredox catalysis is an underdeveloped area.
  • Phosphine organocatalysts are prone to oxidation, forming phosphoranyl radical cations, which hinders their application in photoredox catalysis.

Purpose of the Study:

  • To develop a novel reaction design for dual nucleophilic phosphine photoredox catalysis.
  • To enable the Giese coupling reaction between ynoates and other substrates using this new catalytic system.

Main Methods:

  • A novel reaction design was developed to circumvent the facile oxidation of phosphine organocatalysts.
  • The study employed traditional nucleophilic phosphine organocatalysis in conjunction with photoredox catalysis.
  • Mechanistic investigations included cyclic voltammetry, Stern-Volmer quenching, and interception studies.

Main Results:

  • The developed reaction design successfully avoids the oxidation of the phosphine organocatalyst.
  • The method enables the Giese coupling reaction with ynoates, demonstrating good generality.
  • Mechanistic studies provided support for the proposed reaction pathway.

Conclusions:

  • The study presents a viable strategy for dual nucleophilic phosphine photoredox catalysis.
  • This approach expands the scope of phosphine-catalyzed reactions under photoredox conditions.
  • The findings pave the way for new synthetic methodologies in organic chemistry.