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Related Concept Videos

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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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...
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Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration

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Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

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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.
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Preparation of Alkynes: Alkylation Reaction02:27

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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.
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Updated: Mar 18, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Hydroacenes Made Easy by Gold(I) Catalysis.

Ruth Dorel1, Paul R McGonigal1, Antonio M Echavarren2,3

  • 1Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007, Tarragona, Spain.

Angewandte Chemie (International Ed. in English)
|July 7, 2016
PubMed
Summary

A new method synthesizes partially saturated acene derivatives using gold(I)-catalyzed cyclization. This approach efficiently creates stable polycyclic compounds, extending to nonacene structures.

Keywords:
1,7-enynesSonogashira couplingacenescycloadditiongold(I) catalysis

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Materials Science

Background:

  • Acene derivatives are important in organic electronics.
  • Previous synthesis methods for complex acenes are limited.
  • Partially saturated acenes offer unique electronic properties.

Purpose of the Study:

  • To develop a novel synthetic strategy for partially saturated acene derivatives.
  • To explore the utility of gold(I)-catalyzed reactions in acene synthesis.
  • To access stable polycyclic compounds with extended acene backbones.

Main Methods:

  • Utilized a gold(I)-catalyzed cyclization reaction.
  • Employed 1,7-enynes as starting materials.
  • Characterized the resulting polycyclic products.

Main Results:

  • Successfully synthesized partially saturated acene derivatives.
  • Achieved straightforward access to stable polycyclic products.
  • Extended the synthesis to acene backbones up to nonacene.

Conclusions:

  • The developed gold(I)-catalyzed cyclization is an effective method for synthesizing partially saturated acenes.
  • This strategy provides access to valuable polycyclic compounds for potential applications.
  • The method offers a new route to extended acene structures.