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

Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

3.4K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.4K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

8.7K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
8.7K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

14.3K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
14.3K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

1.9K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
1.9K
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 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

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

Discovery and Characterization of Divarasib (GDC-6036), a Potent Covalent Inhibitor of KRAS G12C.

Journal of medicinal chemistry·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

Preclinical translational physiologically based pharmacokinetic modeling for predicting human pharmacokinetics of proteolysis targeting chimeras: Case studies of vepdegestrant (ARV-471) and bavdegalutamide (ARV-110).

Drug metabolism and disposition: the biological fate of chemicals·2026

Related Experiment Video

Updated: Jul 24, 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

Regioselective aliphatic C-H functionalization using frustrated radical pairs.

Zhipeng Lu1, Minsoo Ju1, Yi Wang1

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

Nature
|July 5, 2023
PubMed
Summary

Frustrated radical pairs (FRPs) enable C-H bond functionalization by cleaving unactivated bonds. Tailoring donor structures allows control over reactivity towards different C-H bonds, offering new synthetic possibilities.

More Related Videos

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

7.9K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.5K

Related Experiment Videos

Last Updated: Jul 24, 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
Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

7.9K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.5K

Area of Science:

  • Organometallic Chemistry
  • Radical Chemistry
  • Organic Synthesis

Background:

  • Frustrated Lewis pairs (FLPs) activate small molecules via heterolytic pathways.
  • Emerging research shows FLPs can form radical pairs through single-electron transfer.
  • Frustrated radical pairs (FRPs) are stable radicals with limited synthetic applications.

Purpose of the Study:

  • To demonstrate C(sp3)-H bond functionalization using a novel class of FRPs.
  • To explore the potential of FRPs as reagents in chemical synthesis.
  • To investigate the tunability of FRP reactivity and regioselectivity.

Main Methods:

  • Generation of FRPs from disilazide donors and N-oxoammonium acceptors.
  • Application of FRPs for the cleavage of unactivated C-H bonds.
  • Mechanistic studies to elucidate the role of radical pairs in the reaction.

Main Results:

  • Successful functionalization of C(sp3)-H bonds yielding aminoxylated products.
  • Demonstration of controlled regioselectivity by modifying donor structures.
  • Evidence supporting the formation and involvement of transient and persistent radical pairs.

Conclusions:

  • FRPs generated from disilazide donors and N-oxoammonium acceptors are effective for C-H bond functionalization.
  • The reactivity of FRPs can be tuned to target primary, secondary, or tertiary C-H bonds.
  • This work expands the synthetic utility of frustrated radical pairs.