Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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...

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.

You might also read

Related Articles

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

Sort by

Same author

Burden and Future Trends of Atopic Dermatitis in the Pediatric Population Aged 19 Years or Younger in 5 East Asian Countries, 1990-2040: A Longitudinal Analysis for the Global Burden of Disease Study 2023.

Dermatitis : contact, atopic, occupational, drug·2026

Same author

Synergistic near-infrared photothermal and electrical stimulation of MgMOF/black phosphorus-reinforced conductive organohydrogels for integrated diagnosis-therapy-repair of complex wounds.

Biomaterials advances·2026

Same author

Phenoxazines with a Phototransferable <i>N</i>-Acetyl Group and Acrylate Linker: Assembly by C-H Activation, Photoconversion to Fluorescent Dyes, Biolabeling, and Super-Resolution Imaging.

Journal of the American Chemical Society·2026

Same author

Case Report: Successful Treatment of Refractory Palmoplantar Pustulosis With Spesolimab and Apremilast.

International journal of rheumatic diseases·2026

Same author

Accelerated Himalayan river meandering and dynamics due to climate change.

Science (New York, N.Y.)·2026

Same author

Enantio- and regioselective nickel/photoredox-catalyzed cross-electrophile coupling of benzylic aziridines with alkynyl bromides.

Science advances·2026

Search research articles

Related Experiment Video

Updated: Jul 7, 2025

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Published on: August 17, 2018

Palladium-Catalyzed Electrooxidative Double C-H Arylation.

Zhipeng Lin^1,2, João C A Oliveira^1,2, Alexej Scheremetjew^1,2

¹Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany.

Journal of the American Chemical Society

|December 27, 2023

Summary

This study introduces an electrochemical palladium-catalyzed method for synthesizing biaryls without chemical oxidants. Mechanistic studies reveal transmetalation between organopalladium complexes is key to this sustainable organic synthesis strategy.

More Related Videos

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

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

Published on: February 16, 2020

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

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

Published on: June 21, 2017

Related Experiment Videos

Last Updated: Jul 7, 2025

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Published on: August 17, 2018

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

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

Published on: February 16, 2020

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

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

Published on: June 21, 2017

Area of Science:

Electrochemistry
Organic Synthesis
Catalysis

Background:

Electrochemical cross-dehydrogenative reactions offer sustainable synthesis but lack mechanistic clarity.
Widespread adoption is hindered by poor understanding of reaction pathways.

Purpose of the Study:

To develop an electrochemical palladium-catalyzed oxidative coupling for biaryl synthesis.
To elucidate the reaction mechanism and identify key factors for success.

Main Methods:

Electrochemical palladium-catalyzed oxidative coupling.
Mechanistic studies including variable time normalization analysis (VTNA), initial rate analysis, H/D exchange, kinetic isotope effect, and organometallic experiments.
Late-stage functionalization and synthesis of Boscalid precursor.

Main Results:

Developed a robust palladaelectrocatalysis for biaryl synthesis, avoiding stoichiometric oxidants.
Suppressed homocoupling and oxygenation, demonstrating compatibility with electron-deficient arenes.
Mechanistic studies confirmed transmetalation between two organopalladium complexes in the turnover-limiting step.

Conclusions:

Matching concentrations or lifetimes of organopalladium intermediates is crucial for electrooxidative catalysis.
Cationic copper(II) stabilizes the palladium(0) catalyst rather than participating in oxidation.
The developed method is practical for late-stage functionalization and precursor synthesis.