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

Reactions at the Benzylic Position: Oxidation and Reduction

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

Radical Oxidation of Allylic and Benzylic Alcohols

Radical Oxidation of Allylic and Benzylic Alcohols

Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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...

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.

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...

You might also read

Related Articles

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

Sort by

Same author

Blood feeding triggers the terminal differentiation of precursor cells in tick salivary glands.

Science advances·2026

Same author

Photoredox Cobalt-Catalyzed Regio- and Stereoselective Reductive Coupling of Alkynes and Pinacol Vinylboronate with Triethylamine as Both an Electron and Hydrogen Donor.

Organic letters·2025

Same author

Role of tankyrase scaffolding in the β-catenin destruction complex and WNT signaling.

bioRxiv : the preprint server for biology·2025

Same author

Regiodivergent Ligand-Controlled Cobalt-Catalyzed Reductive Hydroxymethylation of Alkynes with Aqueous Formaldehyde.

Angewandte Chemie (International ed. in English)·2025

Same author

The STING pathway drives noninflammatory neurodegeneration in NGLY1 deficiency.

The Journal of experimental medicine·2025

Same author

Corrigendum to "Selective degradation of FGFR1/2 overcomes antiestrogen resistance in ER+ breast cancer with FGFR1/2 alterations" [619 1 (2025) 217668 1-13].

Cancer letters·2025

Search research articles

Related Experiment Video

Updated: May 21, 2026

HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin

HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin

Published on: July 23, 2016

A Highly Selective Vanadium Catalyst for Benzylic C-H Oxidation.

Ji-Bao Xia¹, Kevin W Cormier, Chuo Chen

¹Division of Chemistry, Department of Biochemistry, The University of Texas Southwestern Medical Center, Dallas, Texas, 75390, USA; ; Tel: +1 214 6485048.

Chemical Science

|June 20, 2012

Summary

Commercially available vanadium complexes, specifically Cp(2)VCl(2), are effective catalysts for selective benzylic C-H oxidation. This study highlights their potential in C-H activation, avoiding unwanted aromatic oxidation.

More Related Videos

Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

Published on: August 17, 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: May 21, 2026

HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin

HKUST-1 as a Heterogeneous Catalyst for the Synthesis of Vanillin

Published on: July 23, 2016

Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

Tuning the Acidity of Pt/ CNTs Catalysts for Hydrodeoxygenation of Diphenyl Ether

Published on: August 17, 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:

Organometallic Chemistry
Catalysis
Oxidation Reactions

Background:

Vanadium complexes are established catalysts for olefin and alcohol oxidation.
The use of vanadium in C-H oxidation catalysis is less explored.
Selective C-H functionalization remains a significant challenge in organic synthesis.

Purpose of the Study:

To investigate the catalytic potential of vanadium complexes in C-H oxidation reactions.
To evaluate the selectivity and efficacy of Cp(2)VCl(2) in benzylic C-H oxidation.
To explore a novel application of vanadium catalysis beyond traditional oxidation reactions.

Main Methods:

Utilized commercially available bis(cyclopentadienyl)vanadium dichloride (Cp(2)VCl(2)) as the catalyst.
Investigated the catalytic activity in benzylic C-H oxidation reactions.
Analyzed reaction products to determine selectivity and efficiency.

Main Results:

Cp(2)VCl(2) effectively catalyzes benzylic C-H oxidation.
The catalytic system demonstrates high selectivity, avoiding aromatic oxidation.
Successful application of vanadium in selective C-H functionalization was achieved.

Conclusions:

Bis(cyclopentadienyl)vanadium dichloride (Cp(2)VCl(2)) is a potent catalyst for selective benzylic C-H oxidation.
This finding expands the scope of vanadium catalysis in organic synthesis.
The catalyst offers a selective route for C-H functionalization without affecting aromatic rings.