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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.
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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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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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
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Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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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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A General Platform for Copper-Catalyzed Atom Transfer Radical Addition with Electron-Deficient Olefins.

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Organic Letters
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This study introduces a versatile copper-catalyzed platform for atom transfer radical addition (ATRA) reactions. It efficiently synthesizes valuable intermediates from electron-deficient olefins and alkyl halides for further chemical transformations.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Atom transfer radical addition (ATRA) is a crucial reaction in organic synthesis.
  • Developing efficient catalytic systems for ATRA of electron-deficient olefins remains an area of interest.

Purpose of the Study:

  • To establish a broad platform for copper-catalyzed ATRA reactions.
  • To enable the addition of electron-deficient alkyl halides to various electron-deficient olefins.
  • To demonstrate the synthetic utility of the resulting products in subsequent transformations.

Main Methods:

  • Utilized a catalytic system based on Cu(dtbbpy)2(OTf)2.
  • Investigated the radical addition of electron-deficient alkyl halides to acrylates, acrylamides, and vinyl sulfones.
  • Explored telescoped reactions, including nucleophilic substitution and derivatization.

Main Results:

  • Achieved fair to excellent yields for the copper-catalyzed ATRA reactions.
  • Demonstrated the successful synthesis of α-amino esters via substitution with amine nucleophiles.
  • Showcased the preparation of substituted cyclopropanes and γ,δ-unsaturated esters from ATRA products.

Conclusions:

  • The developed copper-catalyzed platform provides a versatile method for ATRA of electron-deficient olefins.
  • The ATRA products serve as valuable intermediates for diverse synthetic applications.
  • This methodology expands the scope of radical additions and offers efficient access to complex molecules.