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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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Introduction
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Radical Substitution: Allylic Bromination01:27

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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Reduction of Alkenes: Catalytic Hydrogenation02:13

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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.
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Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

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Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
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π Molecular Orbitals of the Allyl Cation and Anion01:18

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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 with...
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Updated: Dec 8, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Recent advances in cobalt-catalyzed allylic functionalization.

Jun-Fa Han1, Peng Guo, Xiang-Gui Zhang

  • 1Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), College of Chemistry, Fuzhou University, Fuzhou 350108, China. kyye@fzu.edu.cn.

Organic & Biomolecular Chemistry
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Summary
This summary is machine-generated.

Cobalt catalysis is an emerging, sustainable alternative for allylic substitution reactions. This review covers recent advances in cobalt-catalyzed allylic functionalization, offering valuable insights for synthetic chemists.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Sustainable Chemistry

Background:

  • Cobalt catalysis in allylic substitution has been historically underrepresented compared to other transition metals.
  • Cobalt offers a sustainable, cost-effective alternative due to its abundance.
  • Recent research shows a surge in cobalt's application for allylic functionalization.

Purpose of the Study:

  • To highlight recent advancements in cobalt-catalyzed allylic functionalization.
  • To provide an in-depth discussion of reaction scope and mechanistic insights.
  • To underscore cobalt as a sustainable catalytic option in organic synthesis.

Main Methods:

  • Review of recent literature on cobalt-catalyzed allylic functionalization reactions.
  • Analysis of reaction scope including allylic substitution, nucleophilic allylation, and Heck-type reactions.
  • Examination of mechanistic pathways for key cobalt-catalyzed transformations.

Main Results:

  • Demonstration of cobalt's versatility in various allylic functionalization reactions.
  • Identification of key building blocks synthesized via cobalt catalysis.
  • Elucidation of mechanistic details guiding future catalyst development.
  • Highlighting the sustainability benefits of using earth-abundant cobalt.

Conclusions:

  • Cobalt catalysis is a rapidly developing field in allylic functionalization.
  • Cobalt offers a sustainable and efficient approach to synthesizing valuable organic building blocks.
  • Further exploration of cobalt catalysis promises significant advancements in synthetic chemistry.