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

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.1K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
10.1K
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

9.2K
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal,...
9.2K
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

8.4K
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.
8.4K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.3K
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...
3.3K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.7K
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.
7.7K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K

You might also read

Related Articles

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

Sort by
Same author

Thermal and Photocatalytic Conversion of CO<sub>2</sub> to Ethanol: Advances in Catalyst Design, Challenges, and Opportunities.

ChemSusChem·2026
Same author

Coordination-Driven Direct C─H Metalation of N-Heterocycles With a Superbasic Co(II) Amide Co(TMP)<sub>2</sub>.

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

The Role of Local pH in Electrocatalysis: Measurement, Impact, and Control Strategies.

ACS electrochemistry·2026
Same author

Alkali-Metal Base Catalyzed Electrocyclization of Isoprene Derivatives.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
Same author

Electrochemical CO<sub>2</sub> Reduction on a Bi-Sn Eutectic Alloy in Acidic Media for Formic Acid Production.

ChemSusChem·2026
Same author

Deprotonative C(sp<sup>3</sup>)/C(sp<sup>2</sup>)-H (Multi)Silylation of (Hetero)Arenes Mediated by NaTMP.

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

A Domino-Synthesized Dicoordinate Copper(I) Bis-imidazopyridine Complex Triggering Cuproptosis/Ferroptosis for Enhanced Cancer Immunotherapy.

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

Mirror-Symmetric Organic Two-Dimensional Crystals for Alternative Photon Transport Pathways.

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

Cobalt-Catalyzed Migratory E-Selective Asymmetric Aza-Nozaki-Hiyama-Kishi Coupling.

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

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 journal

Multi-Atom Sub-Nanometer Assemblies on Interpenetrating Multi-Chambered N/C Nanospheres.

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

A Synergistic C<sub>2+</sub> Alcohols/Olefins-Intermediated Pathway Boosts CO<sub>2</sub> Hydrogenation to Aromatics.

Angewandte Chemie (International ed. in English)·2026
See all related articles

Related Experiment Video

Updated: Jun 23, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

7.4K

Alkene Isomerisation Catalysed by a Superbasic Sodium Amide.

Andreu Tortajada1, Gian Luca Righetti1, Ana McGinley2

  • 1Department für Chemie, Biochemie und Pharmacie, Universität Bern, Freiestrasse 3, 3012, Bern, Switzerland.

Angewandte Chemie (International Ed. in English)
|June 17, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces a novel catalytic alkene isomerization method using earth-abundant sodium amide (NaTMP) and PMDETA. This approach efficiently isomerizes various terminal olefins under mild conditions, offering a sustainable alternative to transition metal catalysts.

Keywords:
alkali amidesalkenescatalysisdensity functional theoryisomerization

More Related Videos

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

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

Published on: February 16, 2020

8.2K
Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

7.9K

Related Experiment Videos

Last Updated: Jun 23, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

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

Published on: June 21, 2017

7.4K
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

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

Published on: February 16, 2020

8.2K
Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of &#945;,&#946;-Unsaturated Compounds and Alkynes
05:34

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes

Published on: December 16, 2019

7.9K

Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Alkene isomerization typically relies on transition metals, often requiring harsh conditions or activated substrates.
  • Main group reagents are less explored for alkene isomerization due to limitations with unactivated substrates and high reagent stoichiometry.
  • Developing earth-abundant catalytic systems for alkene isomerization under mild conditions is a significant challenge.

Purpose of the Study:

  • To explore the application of bulky sodium amide (NaTMP) with a Lewis donor (PMDETA) for catalytic alkene isomerization.
  • To investigate the isomerization of unactivated terminal olefins under mild reaction conditions.
  • To elucidate the mechanism and selectivity of the developed catalytic system.

Main Methods:

  • Catalytic alkene isomerization reactions using sodium amide (NaTMP) and N,N,N',N'',N''-pentamethyldiethylenetriamine (PMDETA).
  • Substrate scope evaluation including unactivated olefins, allylamines, and allylethers.
  • Mechanistic investigations employing X-ray crystallography, real-time nuclear magnetic resonance (NMR) monitoring, and density functional theory (DFT) calculations.

Main Results:

  • Successful catalytic isomerization of various terminal olefins, including unactivated ones, under mild conditions.
  • Demonstration of the system's efficacy with allylamines and allylethers, showcasing broad applicability.
  • Mechanistic studies revealed the critical role of in situ-generated TMP(H) and the influence of the alkali metal choice on isomerization efficiency and E/Z selectivity.
  • Isotope exchange and deuteration of unactivated cycloalkenes were achieved, highlighting method versatility.

Conclusions:

  • Bulky sodium amide (NaTMP) partnered with PMDETA provides an efficient catalytic system for alkene isomerization of terminal olefins.
  • The developed method operates under mild conditions and demonstrates broad substrate scope, offering a sustainable alternative to transition metal catalysis.
  • Mechanistic insights clarify the reaction pathway and factors governing selectivity, paving the way for further development in main group-mediated catalysis.