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Related Concept Videos

Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

10.3K
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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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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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 Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.8K
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.
7.8K
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

15.9K
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.
15.9K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.3K
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...
3.3K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.2K
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...
12.2K

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Related Experiment Video

Updated: Jul 17, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Copper-catalyzed propargylic C-H functionalization for allene syntheses.

Dongjie Zhang1, Junjie Fan1, Yaqi Shi1

  • 1Laboratory of Molecular Recognition and Synthesis, Department of Chemistry Zhejiang University Hangzhou Zhejiang 310027 P. R. China masm@sioc.ac.cn.

Chemical Science
|September 1, 2023
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Summary

Researchers synthesized versatile allenenitriles from alkynyl fluorosulfonamides using a novel radical-based C-H functionalization. These compounds serve as key intermediates for creating diverse functionalized heterocycles.

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Methodology Development

Background:

  • Allenenitriles are valuable synthetic intermediates.
  • Efficient synthesis of functionalized allenenitriles remains a challenge.
  • Radical-based C-H functionalization offers a powerful synthetic strategy.

Purpose of the Study:

  • To develop a novel method for synthesizing allenenitriles.
  • To explore the utility of 5-alkynyl fluorosulfonamides in allene synthesis.
  • To demonstrate the first radical-based non-activated propargylic C-H functionalization for allene synthesis.

Main Methods:

  • Reaction of 5-alkynyl fluorosulfonamides under redox neutral conditions.
  • Utilizing radical-based C-H functionalization.
  • Mechanistic studies to elucidate the reaction pathway.

Main Results:

  • Successful synthesis of allenenitriles with diverse functional groups.
  • High yields and excellent chemo- and regio-selectivity achieved.
  • Demonstration of the first radical-based non-activated propargylic C-H functionalization for allene synthesis.

Conclusions:

  • A new, efficient route to versatile allenenitriles has been established.
  • The developed method offers a powerful tool for synthetic chemists.
  • The resulting allenenitriles are readily converted into valuable functionalized heterocycles.