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Related Concept Videos

Radical Formation: Addition00:47

Radical Formation: Addition

1.7K
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...
1.7K
Radical Formation: Overview01:03

Radical Formation: Overview

2.1K
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...
2.1K
Radical Formation: Elimination00:51

Radical Formation: Elimination

1.8K
Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions...
1.8K
Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

4.0K
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
4.0K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

3.6K
A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
3.6K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
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...
2.1K

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Related Experiment Video

Updated: Jul 29, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
10:44

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

Published on: April 19, 2019

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Radical Decarboxylative Carbon-Nitrogen Bond Formation.

Xiangting Li1,2, Xiaobin Yuan1,2, Jiahao Hu2,3

  • 1College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350117, China.

Molecules (Basel, Switzerland)
|May 27, 2023
PubMed
Summary

This review explores radical decarboxylative carbon-nitrogen bond formation, a key strategy for synthesizing complex molecules. It covers various methods using carboxylic acids and their derivatives for efficient bond creation.

Keywords:
C–N bondcarboxylic acidsdecarboxylationmetal catalysisphotocatalysisradicalredox–active

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Carbon-nitrogen bonds are fundamental in numerous natural and synthetic molecules.
  • Radical decarboxylative C-N bond formation offers a versatile synthetic approach.

Purpose of the Study:

  • To provide a comprehensive survey of radical decarboxylative carbon-nitrogen bond formation.
  • To highlight advancements and applications in synthesizing complex molecules.

Main Methods:

  • Review of various radical decarboxylation strategies.
  • Analysis of methods including Barton esters, NHP esters, and MPDOC esters.
  • Discussion of aryliodine(III) dicarboxylates and other related techniques.

Main Results:

  • Demonstrated utility in the synthesis of complex natural products.
  • Compilation of diverse radical decarboxylation methodologies.
  • Elucidation of reaction mechanisms and synthetic applications.

Conclusions:

  • Radical decarboxylative C-N bond formation is a powerful tool in modern synthesis.
  • This review consolidates knowledge and highlights future potential in the field.