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Related Concept Videos

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 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...
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...
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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.

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Biomass Conversion to Produce Hydrocarbon Liquid Fuel Via Hot-vapor Filtered Fast Pyrolysis and Catalytic Hydrotreating
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Fluorous hydrogenation.

Xi Zhao1, Dongmei He, László T Mika

  • 1Department of Biology and Chemistry, City University of Hong Kong, Kowloon, Hong Kong.

Topics in Current Chemistry
|September 29, 2011
PubMed
Summary
This summary is machine-generated.

This review covers fluorous phosphine-modified catalysts used in olefin hydrogenation. These specialized catalysts offer unique advantages for chemical synthesis and industrial applications.

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Area of Science:

  • Catalysis
  • Organometallic Chemistry
  • Green Chemistry

Background:

  • Olefin hydrogenation is a fundamental transformation in organic synthesis.
  • Development of efficient and selective catalysts is crucial for industrial applications.
  • Fluorous chemistry offers unique separation and recycling advantages.

Purpose of the Study:

  • To review the application of fluorous phosphine-modified catalysts in olefin hydrogenation.
  • To highlight the benefits and challenges associated with these catalytic systems.
  • To provide insights into future research directions.

Main Methods:

  • Literature review of studies employing fluorous phosphine-modified catalysts for olefin hydrogenation.
  • Analysis of catalyst performance, including activity, selectivity, and recyclability.
  • Discussion of reaction mechanisms and catalyst design principles.

Main Results:

  • Fluorous phosphine-modified catalysts demonstrate high activity and selectivity in various olefin hydrogenation reactions.
  • The fluorous tag facilitates catalyst separation and recycling, aligning with green chemistry principles.
  • Catalyst stability and reusability are key advantages for sustainable processes.

Conclusions:

  • Fluorous phosphine-modified catalysts represent a promising class of reagents for efficient olefin hydrogenation.
  • Their application contributes to more sustainable and cost-effective chemical synthesis.
  • Further development in catalyst design and reaction optimization is warranted.