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

Covalent Bonding and Lewis Structures02:46

Covalent Bonding and Lewis Structures

Compared to ionic bonds, which results from the transfer of electrons between metallic and nonmetallic atoms, covalent bonds result from the mutual attraction of atoms for a “shared” pair of electrons.
Lewis Symbols and the Octet Rule02:36

Lewis Symbols and the Octet Rule

Chemical bonds are complex interactions between two or more atoms or ions, which reduce the potential energy of the molecule. Gilbert N. Lewis developed a model called the Lewis model that simplified the depiction of chemical bond formation and provided straightforward explanations for the chemical bonds seen in most common compounds.
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the surface of...
Lewis Acids and Bases02:33

Lewis Acids and Bases

In 1923, G. N. Lewis proposed a generalized definition of acid-base behavior in which acids and bases are identified by their ability to accept or to donate a pair of electrons and form a coordinate covalent bond.
A coordinate covalent bond (or dative bond) occurs when one of the atoms in the bond provides both bonding electrons. For example, a coordinate covalent bond occurs when a water molecule combines with a hydrogen ion to form a hydronium ion. A coordinate covalent bond also results when...
Lewis Acids and Bases02:16

Lewis Acids and Bases

This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...
Lewis Structures of Molecular Compounds and Polyatomic Ions02:54

Lewis Structures of Molecular Compounds and Polyatomic Ions

To draw Lewis structures for complicated molecules and molecular ions, it is helpful to follow a step-by-step procedure as outlined:

You might also read

Related Articles

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

Sort by
Same author

Synthetic routes to PN<sub>2</sub>C<sub>2</sub>-heterocyclic cations.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Synthesis and Isolation of α-Diazophosphonium Ylides.

Journal of the American Chemical Society·2026
Same author

Reactions of phosphazines with primary and secondary boranes: adducts, rings and reduction.

Chemical communications (Cambridge, England)·2026
Same author

Beyond FLP additions: FLP deprotonation and C-O bond cleavage of aliphatic, aryl and ester derived olefins.

Chemical communications (Cambridge, England)·2026
Same author

An Intramolecular Lewis Adduct with Diverse FLP Reactivity.

Inorganic chemistry·2026
Same author

B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed Dearomative [2π+2σ] Cycloaddition of 1-Naphthols with Bicyclo[1.1.0]butanes.

Organic letters·2025
Same journal

Catalytic synthesis of saturated azacycles using transborylation.

Organic & biomolecular chemistry·2026
Same journal

Pyridines with adamantane fragments and their 1,2,4-triazine analogues as anti-quorum-sensing agents, synthesis and molecular docking.

Organic & biomolecular chemistry·2026
Same journal

Synthesis of polymethylene-linked bis(cyclobutane-fused chromanones) mediated by gold photocatalysis.

Organic & biomolecular chemistry·2026
Same journal

Palladium-catalyzed chelation-assisted C-H functionalization of quinoline aldehydes to esters with mechanistic insights.

Organic & biomolecular chemistry·2026
Same journal

One-pot metal-free access to uracil-benzofuran bis-heterocycles: synthesis and DFT insights.

Organic & biomolecular chemistry·2026
Same journal

Transition-metal-free three-component synthesis of α-tertiary trifluoromethyl phosphonates from CF<sub>3</sub> diazo compounds.

Organic & biomolecular chemistry·2026
See all related articles

Related Experiment Video

Updated: May 23, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

"Frustrated Lewis pair" hydrogenations.

Douglas W Stephan1

  • 1Department of Chemistry, University of Toronto, 80 St George St, Toronto, Ontario, Canada M5S3H6. dstephan@chem.utoronto.ca

Organic & Biomolecular Chemistry
|April 17, 2012
PubMed
Summary
This summary is machine-generated.

Metal-free hydrogenation catalysts using frustrated Lewis pairs (FLPs) have advanced significantly. These systems offer promising applications for various reductions, including aromatic compounds, presenting sustainable alternatives in catalysis.

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

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

Related Experiment Videos

Last Updated: May 23, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
07:49

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

Published on: February 20, 2020

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

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

Area of Science:

  • Catalysis
  • Organic Chemistry
  • Sustainable Chemistry

Background:

  • Traditional hydrogenation often relies on precious or toxic metals.
  • Frustrated Lewis pairs (FLPs) offer a metal-free alternative for activating small molecules like H2.
  • Developing efficient metal-free catalysts is crucial for sustainable chemical synthesis.

Purpose of the Study:

  • To review recent developments in metal-free hydrogenation catalysts based on FLP systems.
  • To highlight the diverse applications of FLP-mediated reductions.
  • To explore the potential of these sustainable catalytic methods.

Main Methods:

  • Discussion of catalyst designs based on FLP principles.
  • Review of applications in the reduction of various organic substrates.
  • Analysis of FLP-mediated aromatic reductions.

Main Results:

  • A range of metal-free FLP catalysts have been developed.
  • Successful applications demonstrated for the reduction of imines, aziridines, enamines, silyl enol ethers, diimines, metallocene derivatives, and nitrogen-based heterocycles.
  • Efficient aromatic reduction of aniline derivatives to cyclohexylamine analogs achieved using FLPs.

Conclusions:

  • Metal-free hydrogenation using FLP systems is a rapidly advancing field.
  • These catalysts provide effective and sustainable routes for numerous organic reductions.
  • FLPs hold significant potential for future catalytic applications, minimizing reliance on metal catalysts.