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

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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...
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 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...

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Related Experiment Video

Updated: May 15, 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 mediated hydrogenations.

Douglas W Stephan1, Gerhard Erker

  • 1Department of Chemistry, University of Toronto, ON, Canada. dstephan@chem.utoronto.ca

Topics in Current Chemistry
|January 2, 2013
PubMed
Summary

Frustrated Lewis pairs (FLPs) are developed as efficient reductants for organic hydrogenation. These FLPs demonstrate utility in both stoichiometric and catalytic applications, offering a novel approach to chemical reductions.

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Frustrated Lewis pairs (FLPs) represent a unique class of Lewis acid-base adducts that remain unquenched.
  • FLPs have emerged as powerful tools in small molecule activation and catalysis.

Purpose of the Study:

  • To describe the development of FLPs as stoichiometric and catalytic reductants.
  • To showcase the application of FLPs in the hydrogenation of diverse organic substrates.

Main Methods:

  • Synthesis and characterization of novel FLP systems.
  • Application of FLPs in hydrogenation reactions under various conditions.
  • Evaluation of catalytic efficiency and substrate scope.

Main Results:

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  • Demonstrated successful hydrogenation of a variety of organic substrates using FLPs.
  • Established FLPs as effective stoichiometric and catalytic reductants.
  • Achieved high yields and selectivities in FLP-mediated hydrogenations.

    • Conclusions:

    • FLPs are versatile reagents for organic hydrogenation.
    • This work expands the scope of FLP applications in reductive catalysis.
    • The developed FLP systems offer a sustainable alternative for hydrogenation processes.