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 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

2.7K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
2.7K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

2.6K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
2.6K
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

9.3K
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.
9.3K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

7.3K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
7.3K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

17.0K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
17.0K
π Molecular Orbitals of the Allyl Cation and Anion01:18

π Molecular Orbitals of the Allyl Cation and Anion

3.5K
An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each...
3.5K

You might also read

Related Articles

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

Sort by
Same author

Enantioselective synthesis of configurationally stable [5]helicenes containing 1,2-azaborine units.

Chemical science·2026
Same author

Correction: Bis(amidophenolate)-supported pnictoranides: Lewis acid-induced electromerism in a bismuth complex.

Chemical science·2026
Same author

Synthesis and reactivity of a strongly pyramidalized P(III)-compound embedded into a pyrrolide (ONO)<sup>3-</sup> pincer ligand.

Chemical communications (Cambridge, England)·2026
Same author

A Diazo-free Equivalent of the Unsubstituted Carbyne Cation: Straightforward Synthesis of Naphthalenes and Pyridines via [<sup>12/13</sup>CH]<sup>+</sup> Insertion.

Journal of the American Chemical Society·2026
Same author

Enantioselective synthesis and racemization dynamics of trithia[5]helicenes derived from the dithieno[2,3-<i>b</i>:3',2'-<i>d</i>]-thiophene unit.

Chemical science·2025
Same author

Bis(amidophenolate)-supported pnictoranides: Lewis acid-induced electromerism in a bismuth complex.

Chemical science·2025
Same journal

Symmetry Breaking in Achiral Porphyrins: Noncovalent Origins of Emergent Optical Activity.

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

Modulation of O<sub>2</sub> Affinity and Enzymatic Activity of Core‒Shell Structured Hemoglobin Nanoparticles.

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

Stepwise Synthesis of Tetrabenzotriazaporphyrins (TBTAPs) and Their Open 2- and 3-Ring Fragments.

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

Geometry-Based Neural-Network Prediction of Electron Localization Function Topology in Dense Hydrogen.

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

Dual Regulation of Charge Carriers Based on Phosphorus-Doped CdS/Nickel Polyphthalocyanine Dyads for Boosting Photocatalytic CO<sub>2</sub> Reduction.

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

Effects of Biotin on a Fluorescein-Based Photosensitizer Revealed by Multiscale Computational Modeling.

Chemistry (Weinheim an der Bergstrasse, Germany)·2026
See all related articles

Related Experiment Video

Updated: Apr 28, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

7.3K

α-Cationic phosphines: synthesis and applications.

Manuel Alcarazo1

  • 1Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 41470 Mülheim an der Ruhr (Germany). alcarazo@kofo.mpg.de.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 4, 2014
PubMed
Summary
This summary is machine-generated.

Cationic phosphine ligands, often overlooked in catalysis, offer superior π-acceptor properties. These ligands enhance metal Lewis acidity, leading to highly effective catalysts for various transformations.

Keywords:
coordination modesligand designphosphorustransition metals

More Related Videos

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

11.1K
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

10.3K

Related Experiment Videos

Last Updated: Apr 28, 2026

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI
08:46

Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of PhosphorusI

Published on: November 22, 2016

7.3K
The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
10:51

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

11.1K
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

10.3K

Area of Science:

  • Coordination Chemistry
  • Organometallic Chemistry
  • Catalysis

Background:

  • Ancillary ligands in coordination chemistry are typically anionic or neutral.
  • Cationic ligands are rare, with charged groups usually distant from the donor atom.

Purpose of the Study:

  • To highlight the overlooked potential of cationic phosphines in catalysis.
  • To discuss their unique electronic properties and applications.

Main Methods:

  • Review of recent experimental and theoretical studies.
  • Analysis of the π-acceptor character and Lewis acidity enhancement.

Main Results:

  • Cationic phosphines exhibit strong π-acceptor capabilities, surpassing phosphites and polyfluorinated phosphines.
  • This property enhances the Lewis acidity of coordinated metals.
  • Novel Pt(II) and Au(I) catalysts demonstrate superior performance.

Conclusions:

  • Cationic phosphines with direct positive charge are highly effective ligands.
  • They represent a promising avenue for developing advanced catalytic systems.