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Radical Reactivity: Nucleophilic Radicals

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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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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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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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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Redox Neutral Radical-Relay Nickel-Catalyzed Remote Carbonylation.

Ming Li1, Fan Gao1, Dong-Yu Miao1

  • 1College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, P. R. China.

Organic Letters
|March 29, 2023
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Summary
This summary is machine-generated.

A new nickel-catalyzed reaction efficiently installs carbonyl groups using remote radical coupling. This method provides site-selective α-substituted ketones under mild, redox-neutral conditions.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carbonyl group installation is crucial in organic synthesis.
  • Existing methods for α-substituted ketone synthesis often require harsh conditions or lack selectivity.
  • Remote functionalization strategies are highly sought after for efficient molecular construction.

Purpose of the Study:

  • To develop a novel and efficient method for catalytic carbonyl group installation.
  • To achieve α-substituted ketone synthesis via remote radical coupling.
  • To establish a reaction with broad functional-group compatibility and high site-selectivity.

Main Methods:

  • Nickel-catalyzed reaction employing sequential single-electron transfer and 1,5-hydrogen atom transfer.
  • Remote radical coupling mechanism for carbonyl insertion.
  • Optimization of reaction conditions including pressure and redox environment.

Main Results:

  • Successful catalytic installation of a carbonyl group at the remote position.
  • Formation of α-substituted ketones with high yields and selectivity.
  • Demonstration of functional-group tolerance under mild, redox-neutral conditions.

Conclusions:

  • The developed nickel-catalyzed method offers an efficient and selective route to α-substituted ketones.
  • The reaction proceeds via a unique remote radical coupling pathway.
  • This methodology expands the toolkit for strategic carbonyl group introduction in complex molecules.