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

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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 reactions,...

You might also read

Related Articles

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

Sort by
Same author

Magnetic Nanoparticles as a Theranostic Platform in Brain Tumor Treatment: Surmounting the Bench-to-Bedside Barriers.

International journal of nanomedicine·2026
Same author

Stage-specific disruption of erythropoiesis leads to anemia in newly diagnosed multiple myeloma patients.

Frontiers in cell and developmental biology·2026
Same author

Cancer diagnosis method based on multi-spectral diffraction imaging for cell recognition.

Biosensors & bioelectronics·2026
Same author

Ethical considerations and management strategies for fertility preservation in women of reproductive age with malignant tumors: Chinese practices and perspectives.

Frontiers in endocrinology·2026
Same author

Boronyl Radical-Catalyzed Intermolecular (4 + 2) Cycloaddition of Cyclobutanes and Alkenes: Synthesis of Polysubstituted Cyclohexanes.

The Journal of organic chemistry·2026
Same author

Advances in Double-Stranded DNA Targeting Technologies.

Exploration (Beijing, China)·2026

Related Experiment Video

Updated: Jun 12, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Tetrahydroxydiboron-Driven Photocatalytic Three-Component Reductive Petasis Reaction.

Weibin Xie1, Wei Wei1, Shihui Wang2

  • 1State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300071, China.

The Journal of Organic Chemistry
|June 11, 2026
PubMed
Summary

This study introduces a new method for synthesizing N-arylated-α-amino acid derivatives using a three-component reaction. Tetrahydroxydiboron acts as a reducing agent, enabling mild reaction conditions and broad substrate scope for valuable compounds.

More Related Videos

Synthesis and Performance Evaluations of ZnCoS/ZnCdS with Twin Crystal Structure for Multifunctional Redox Photocatalysis in Energy Applications
09:22

Synthesis and Performance Evaluations of ZnCoS/ZnCdS with Twin Crystal Structure for Multifunctional Redox Photocatalysis in Energy Applications

Published on: July 25, 2025

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

Related Experiment Videos

Last Updated: Jun 12, 2026

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
09:12

[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Synthesis and Performance Evaluations of ZnCoS/ZnCdS with Twin Crystal Structure for Multifunctional Redox Photocatalysis in Energy Applications
09:22

Synthesis and Performance Evaluations of ZnCoS/ZnCdS with Twin Crystal Structure for Multifunctional Redox Photocatalysis in Energy Applications

Published on: July 25, 2025

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Photocatalysis

Background:

  • N-arylated-α-amino acid derivatives are crucial building blocks in pharmaceuticals and biologically active molecules.
  • Efficient synthetic routes are needed to access these important compounds.

Purpose of the Study:

  • To develop a novel, mild, and efficient method for synthesizing N-arylated-α-amino acid derivatives.
  • To explore the utility of tetrahydroxydiboron in photocatalytic three-component reactions.

Main Methods:

  • A photocatalytic three-component reductive Petasis reaction involving aryl amines, glyoxalates, and activated esters of aliphatic acids.
  • Utilizing tetrahydroxydiboron as a reducing agent under mild conditions.

Main Results:

  • Successful synthesis of various N-arylated-α-amino acid derivatives.
  • Demonstrated broad substrate scope and mild reaction conditions.
  • Mechanistic studies elucidated the role of tetrahydroxydiboron in radical generation and imine addition.

Conclusions:

  • The developed method provides a facile and efficient route to N-arylated-α-amino acid derivatives.
  • Tetrahydroxydiboron serves as a practical reducing agent in this photocatalytic transformation.
  • This approach offers a valuable tool for organic synthesis.