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Related Concept Videos

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...
12.6K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.4K
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...
3.4K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.9K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
1.9K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.7K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.7K
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

4.0K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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Updated: Sep 15, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Transition-metal-catalyzed alkene-relayed intermolecular C-H activation.

Qiongqiong Zhu1, Ming-Shun Mei1, Xiang Zuo1

  • 1School of Chemical Science and Engineering, Shanghai Key Laboratory of Chemical Assessment and Sustainability, Tongji University, Shanghai 200092, China. zhangyanghui@tongji.edu.cn.

Chemical Communications (Cambridge, England)
|July 18, 2025
PubMed
Summary

Alkene-relayed C-H activation offers a novel approach to C-H functionalization, where alkenes act as both relays and carbon synthons. This dual role significantly expands synthetic possibilities in transition-metal catalysis.

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • C-H activation is a cornerstone of modern organic synthesis.
  • Alkene-relayed C-H functionalization presents a unique strategy for incorporating alkenes into complex molecules.
  • Intermolecular reactions utilizing alkenes as both activators and building blocks are highly sought after.

Purpose of the Study:

  • To systematically review and categorize alkene-relayed C-H functionalization reactions.
  • To provide mechanistic insights into these transformations.
  • To highlight current challenges and future research directions in this field.

Main Methods:

  • Comprehensive literature survey of alkene-relayed C-H functionalization reactions.
  • Categorization based on alkene type, metal catalyst, and reaction class.
  • Analysis of mechanistic pathways for key examples.

Main Results:

  • A systematic summary of diverse alkene-relayed C-H functionalization reactions.
  • Detailed mechanistic explanations for selected transformations.
  • Identification of trends and patterns in catalyst and substrate scope.

Conclusions:

  • Alkene-relayed C-H activation is a powerful and versatile synthetic strategy.
  • The dual role of alkenes as relays and synthons broadens synthetic applications.
  • Further research is needed to address current challenges and unlock new possibilities.