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

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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...

Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.

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...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

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.

Radical Anti-Markovnikov Addition to Alkenes: Overview

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.

You might also read

Related Articles

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

Sort by

Same author

A metal-DNA biohybrid as enantioselective artificial photoDNAzyme.

Nature communications·2026

Same author

Bioinspired total synthesis of (dibromo)sceptrin and (dibromo)ageliferin.

Chemical communications (Cambridge, England)·2026

Same author

Unified, catalyst-controlled, bioinspired total synthesis of dimeric piperine alkaloids in batch and flow.

Chemical communications (Cambridge, England)·2026

Same author

Synthesis of optically active cyclopropanes by functionalization of cyclopropenes.

Organic & biomolecular chemistry·2026

Same author

Late-Stage Oxygenation in Organic Synthesis: From Innate Reactivity to Directed Selectivity in Complex Settings.

Angewandte Chemie (International ed. in English)·2026

Same author

Copper-catalyzed allylic substitution of nitroallyl derivatives with Grignard reagents.

Chemical communications (Cambridge, England)·2026

Search research articles

Related Experiment Video

Updated: Jun 27, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Catalyst-Controlled Regiodivergent C-H Olefination of Furanyl Carbamates through a Rational Approach.

François Richard¹, Morgan Languet², Cora Escande de Messières¹

¹Queen Mary University of London, Department of Chemistry, Mile End Road, London E1 4NS, UK.

|June 26, 2026

Summary

Researchers developed a new method for selective C-H olefination of heteroarenes. This catalyst-controlled strategy allows precise regioselective functionalization at either the C3 or C5 position, offering a versatile synthetic platform.

Keywords:

C−H activation DFT catalyst control furan olefination pyrrole regiodivergent rhodium catalysis thiophene

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO₂ Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

Related Experiment Videos

Last Updated: Jun 27, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

Published on: February 7, 2019

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Versatile CO₂ Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

Area of Science:

Synthetic organic chemistry
Heteroarene functionalization
Catalysis

Background:

Selective functionalization of heteroarenes is crucial due to their prevalence in pharmaceuticals.
Existing olefination methods for five-membered heteroarenes often lack precise regioselectivity control.

Purpose of the Study:

To develop a regioselective C-H olefination strategy for heteroarenes.
To enable precise control over functionalization at either the C3 or C5 position.

Main Methods:

Density Functional Theory (DFT) supported computational studies.
Catalyst-controlled C-H olefination reactions.
Utilized cyclic dienol carbamates as substrates.

Main Results:

Achieved regioselective C-H olefination of cyclic dienol carbamates.
Demonstrated control to access either C3- or C5-substituted heteroarenes.
Validated the strategy through DFT calculations and experimental results.

Conclusions:

The reported strategy offers a rational and versatile platform for regioselective heteroarene functionalization.
This method enhances synthetic control in accessing valuable substituted heteroarene compounds.
Advances the field of targeted molecular synthesis for drug discovery and materials science.