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

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

4.0K
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...
4.0K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

9.4K
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.
9.4K
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

6.4K
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...
6.4K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.8K
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...
2.8K
Catalysis02:50

Catalysis

32.1K
The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
32.1K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.4K
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.
2.4K

You might also read

Related Articles

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

Sort by
Same author

Facile Synthesis of α,ω-Dihydroxy Telechelic Macromonomers From Ethylene and α-Olefins for Recyclable Alternating Block Copolymers.

Angewandte Chemie (International ed. in English)·2026
Same author

Divergent Transformations of Cobaltacyclobutenes Generated from [2 + 2]-Cycloadditions of Vinylidenes and Alkynes.

ACS catalysis·2026
Same author

A Catalytically Generated Transition Metal Analog of the Simmons-Smith Reagent.

Tetrahedron·2026
Same author

Application of Asymmetric Catalysis in the <i>E</i>/<i>Z</i>-Stereodivergent Synthesis of Alkenes.

Journal of the American Chemical Society·2025
Same author

Catalytic Reductive Annulation Reactions of Alkenes Using Dihaloalkanes.

Tetrahedron letters·2025
Same author

Catalytic Asymmetric Synthesis of Axially Chiral Methylenecyclopropanes.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Mar 26, 2026

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

8.7K

Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes.

You-Yun Zhou1, Christopher Uyeda2

  • 1Department of Chemistry, Purdue University, 560 Oval Dr., West Lafayette, IN, 47907, USA.

Angewandte Chemie (International Ed. in English)
|January 30, 2016
PubMed
Summary
This summary is machine-generated.

Dinuclear nickel complexes catalyze reductive cyclopropanation using dichloromethane. Mild reductants and diverse alkenes are tolerated, enabling new carbene transformations from oxidized methylene sources.

Keywords:
alkenescarbene transfercyclopropanationnickel catalysisreductive cycloaddition

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

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

Published on: November 9, 2019

8.5K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

26.0K

Related Experiment Videos

Last Updated: Mar 26, 2026

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
05:48

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

8.7K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

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

Published on: November 9, 2019

8.5K
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
11:44

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

26.0K

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Catalytic carbene transformations are crucial in organic synthesis.
  • Developing efficient and selective methods for cyclopropanation remains a key challenge.
  • Nickel catalysis offers a sustainable alternative to precious metal catalysts.

Purpose of the Study:

  • To develop a novel dinuclear nickel catalyst for the reductive cyclopropanation of alkenes.
  • To utilize dichloromethane as a methylene source in a catalytic process.
  • To investigate the functional group tolerance and substrate scope of the developed catalytic system.

Main Methods:

  • Synthesis and characterization of dinuclear nickel complexes supported by naphthyridine-diimine (NDI) ligands.
  • Optimization of reaction conditions, including reductants (Zn or Et2Zn) and solvents.
  • Evaluation of catalyst performance with a range of structurally diverse alkenes.

Main Results:

  • Dinuclear Ni-NDI complexes efficiently catalyze the reductive cyclopropanation of alkenes with CH2Cl2.
  • The catalytic system demonstrates high functional group tolerance due to mild terminal reductants.
  • Structurally and electronically diverse alkenes are successfully transformed into cyclopropanes.
  • Mononickel catalysts show significantly lower yields (≤20%).

Conclusions:

  • Dinuclear nickel complexes represent a powerful new class of catalysts for reductive cyclopropanation.
  • This work provides a novel entry into catalytic carbene transformations using oxidized methylene precursors.
  • The developed methodology offers a sustainable and versatile route to cyclopropane derivatives.