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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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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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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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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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Alkene 1,2-Difunctionalization by Radical Alkenyl Migration.

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  • 1Westfälische Wilhelms-Universität, Organisch-Chemisches Institut, Corrensstraße 40, 48149, Münster, Germany.

Angewandte Chemie (International Ed. in English)
|November 23, 2017
PubMed
Summary

This study introduces a transition-metal-free method for radical perfluoroalkylation and alkenylation of unactivated alkenes. The novel cascade reaction utilizes electron catalysis and alkenyl migration on allylic alcohols.

Keywords:
alkenesalkenyl migrationalkenylationperfluoroalkylationsingle-electron transfer

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Area of Science:

  • Organic Chemistry
  • Radical Reactions
  • Catalysis

Background:

  • Perfluoroalkylation and alkenylation are important synthetic transformations.
  • Developing transition-metal-free methods is a key goal in sustainable chemistry.
  • Radical cascade reactions offer efficient pathways for complex molecule synthesis.

Purpose of the Study:

  • To develop a novel transition-metal-free method for simultaneous α-perfluoroalkylation and β-alkenylation.
  • To investigate the mechanism of radical cascade reactions involving alkenyl migration.
  • To utilize readily accessible allylic alcohols as starting materials.

Main Methods:

  • Radical cascade reaction initiated by perfluoroalkyl radical addition.
  • Employing electron catalysis for the reaction cascade.
  • Utilizing 1,4- or 1,5-alkenyl migration pathways.
  • Generating ketyl radical anions to sustain the reaction chain.

Main Results:

  • Achieved transition-metal-free α-perfluoroalkylation and vicinal β-alkenylation of unactivated alkenes.
  • Demonstrated regioselective perfluoroalkyl radical addition.
  • Elucidated the mechanism involving alkenyl migration and ketyl radical anion formation.
  • Showcased the utility of allylic alcohols as versatile substrates.

Conclusions:

  • The developed method provides an efficient and sustainable route for synthesizing complex organofluorine compounds.
  • The reaction mechanism highlights the importance of alkenyl migration and single-electron-transfer processes.
  • This work expands the toolkit for radical-mediated functionalization of alkenes.