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

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 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...

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...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

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.

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

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

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...

You might also read

Related Articles

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

Sort by

Same author

Discomfort of noninvasive ventilation, high flow nasal cannula oxygen, and conventional oxygen implemented after extubation in non-COPD patients.

Critical care (London, England)·2026

Same author

Unveiling the role of air pollution in diabetic kidney disease: an integrated study combining network toxicology, machine learning, and Mendelian randomization.

Renal failure·2026

Same author

Impact of Concurrent Graft-versus-Host Disease on Long-Term Survival in Critically Ill Patients Following Allogeneic Hematopoietic Stem Cell Transplantation for Hematological Malignancies.

Transplantation and cellular therapy·2026

Same author

A relay energy transfer paradigm for asymmetric photocatalyzed [4+2] cycloadditions.

Science (New York, N.Y.)·2026

Same author

Serpine1 regulates Th17 cell differentiation and exacerbates IMQ-induced skin inflammation.

Journal of immunology (Baltimore, Md. : 1950)·2026

Same author

Effects of hydromorphone for patient-controlled intravenous analgesia on postpartum depression and sleep disorders after cesarean section: a randomized, double-blind controlled trial.

Frontiers in pharmacology·2026

Search research articles

Related Experiment Video

Updated: Oct 25, 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

Organocatalyst-controlled site-selective arene C-H functionalization.

Jian-Hui Mao¹, Yong-Bin Wang², Limin Yang³

¹Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, China.

Nature Chemistry

|August 10, 2021

Summary

This summary is machine-generated.

This study introduces a new organocatalyst method for site-selective arene C-H functionalization, enabling the creation of chiral molecules. This breakthrough offers a general strategy for controlled para-selective functionalization of aryl C-H bonds.

More Related Videos

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

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

Related Experiment Videos

Last Updated: Oct 25, 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

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

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

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Organocatalysis is a key tool for synthesizing chiral molecules.
Functionalizing unreactive aryl C-H bonds with site- and enantioselectivity is challenging.
Existing methods have limitations in achieving selective arene C-H functionalization.

Purpose of the Study:

To develop an organocatalyst-controlled strategy for para-selective arene C-H functionalization.
To address the limitations in site- and enantioselective functionalization of inactive aryl C-H bonds.
To provide a general protocol for controlled arene C-H functionalization.

Main Methods:

Utilized a chiral phosphoric acid catalyst to emulate enzyme catalysis.
Employed catalyst-controlled para-selectivity for arene C-H functionalization.
Investigated the compatibility with various nucleophiles.

Main Results:

Achieved over 100 para-selective adducts with stereodefined centers or axes.
Demonstrated control over chemo- and site-selectivity through catalyst design.
Successfully functionalized inactive aryl C-H bonds with high selectivity.

Conclusions:

Presented a novel organocatalyst-controlled para-selective arene C-H functionalization strategy.
The method provides a general approach for controlled functionalization of aryl C-H bonds.
This work expands the synthetic toolbox for creating complex chiral molecules.