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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.0K
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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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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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 Formation: Addition00:47

Radical Formation: Addition

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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.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
1.8K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

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This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
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Radical Reactivity: Intramolecular vs Intermolecular01:33

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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...
1.8K
Radical Formation: Overview01:03

Radical Formation: Overview

2.2K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
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Electrochemical Single-Carbon Insertion via Distonic Radical Cation Intermediates.

Tatsuya Morimoto1, Yoshio Nishimoto2, Taku Suzuki-Osborne3

  • 1Department of Chemistry and Life Science, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan.

Journal of the American Chemical Society
|July 14, 2025
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This study introduces a new electrochemical method for single-carbon insertion into aromatic compounds, specifically pyridines. The novel approach utilizes pyrrole derivatives and diazo compounds for efficient synthesis of complex molecules.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Medicinal Chemistry

Background:

  • Polysubstituted (hetero)aromatic compounds are crucial building blocks in pharmaceuticals.
  • Efficient synthesis of these compounds is vital for drug discovery and development.
  • Existing methods for carbon insertion often lack selectivity or require harsh conditions.

Purpose of the Study:

  • To develop a novel electrochemical method for single-carbon insertion into (hetero)aromatic compounds.
  • To specifically target the synthesis of polysubstituted pyridine derivatives.
  • To investigate the mechanism and control of regioselectivity in the carbon insertion process.

Main Methods:

  • Electrochemical oxidation of pyrrole derivatives to generate radical cation intermediates.
  • Nucleophilic attack of diazo compounds on the radical cation intermediates.
  • Employing *in situ* spectroscopy and theoretical calculations to elucidate reaction mechanisms.
  • Modulating *N*-protecting groups to control the position of carbon insertion.

Main Results:

  • A novel electrochemical method for single-carbon insertion into pyridines was established.
  • Polysubstituted pyridine derivatives were synthesized with high efficiency.
  • Unprecedented *para*-selective insertion was achieved by using electron-withdrawing *N*-protecting groups.
  • Distonic radical cation intermediates were identified as key species in the reaction mechanism.

Conclusions:

  • The developed electrochemical method offers a versatile and efficient route for synthesizing polysubstituted (hetero)aromatic compounds.
  • The study provides new mechanistic insights into single-carbon insertion chemistry.
  • This work expands the synthetic toolbox for medicinal chemists and organic synthesis.