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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.
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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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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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In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...
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Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
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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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Copper-Catalyzed Trifluoromethylalkynylation via Radical-Mediated Multicomponent Process.

Mai Zhang1, Jia Ni1, Mengtao Ma1

  • 1Department of Chemistry and Materials Science, College of Science, Nanjing Forestry University, Nanjing, China.

Chemistry, an Asian Journal
|November 29, 2025
PubMed
Summary

This study introduces a copper-catalyzed reaction for synthesizing complex molecules. The efficient method uses Togni

Keywords:
copper catalysisradical‐mediatedtrifluoromethylalkynylationβ‐trifluoromethylated propynes

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Multicomponent reactions (MCRs) are essential for efficient molecular assembly.
  • Developing new MCRs expands synthetic capabilities for complex molecule construction.

Purpose of the Study:

  • To develop an efficient copper-catalyzed multicomponent reaction.
  • To synthesize β-trifluoromethyl propynes with high regioselectivity.

Main Methods:

  • Utilized Togni's reagent II, alkenes, and alkynes in a copper-catalyzed process.
  • Employed mild reaction conditions to promote chemoselectivity and regioselectivity.

Main Results:

  • Achieved efficient synthesis of β-trifluoromethyl propynes.
  • Demonstrated high regioselectivity in the trifluoromethylalkynylation of alkenes.
  • Showcased broad substrate scope and excellent functional group tolerance.

Conclusions:

  • The developed method offers a practical and efficient route to valuable trifluoromethylated compounds.
  • This copper-catalyzed radical process is a versatile tool for organic synthesis.