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Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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.
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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.
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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Related Experiment Video

Updated: Jun 29, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Visible Light-Induced Alkyne-Carbonyl Metathesis in Multicomponent Reactions.

Pan Pan1, Zhuang-Chao Fang2, Fang-Xin Wang3

  • 1Biomass Oligosaccharides Engineering Technology Research Center of Anhui Province, Engineering Research Center of Biomass Conversion and Pollution Prevention of Anhui Educational Institutions, School of Chemical and Material Engineering, Fuyang Normal University, Fuyang, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 27, 2026
PubMed
Summary

Visible light-induced alkyne-carbonyl metathesis (ACM) integrated into multicomponent reactions offers an efficient pathway for synthesizing functional aldehydes and ketones. This approach enhances atom economy and enables complex molecule construction under mild conditions.

Keywords:
Paternò–Büchi reactionalkyne–carbonyl metathesismulticomponent reactionp‐quinone methidevisible light

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

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Last Updated: Jun 29, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
09:37

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Synthetic Methodology

Background:

  • Visible light-induced alkyne-carbonyl metathesis (ACM) is crucial for synthesizing α, β-unsaturated carbonyl compounds.
  • Visible light-induced multicomponent reactions are vital for creating complex molecular architectures efficiently.
  • Integrating ACM into multicomponent reactions presents a novel synthetic strategy.

Purpose of the Study:

  • To review the progress of visible light-induced multicomponent reactions involving p-quinone methide (p-QM) intermediates generated by ACM.
  • To explore the application of this strategy in both racemic and asymmetric synthesis.
  • To discuss substrate scope, reaction mechanisms, limitations, and future directions.

Main Methods:

  • Summarizing visible light-induced multicomponent coupling reactions of alkynes, quinones, and nucleophiles.
  • Reviewing asymmetric synthesis applications.
  • Analyzing reaction mechanisms and substrate scope.

Main Results:

  • Demonstrated efficient synthesis of functional aldehydes/ketones via ACM-driven multicomponent reactions.
  • Highlighted applications in racemic and asymmetric synthesis of complex molecules.
  • Identified key reaction parameters and mechanistic insights.

Conclusions:

  • Visible light-induced ACM-based multicomponent reactions provide an efficient and atom-economical route to functionalized carbonyl compounds.
  • This strategy is versatile, applicable to both racemic and asymmetric synthesis of complex chiral molecules.
  • Further research is needed to address current limitations and expand future applications.