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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.6K
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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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

7.1K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
7.1K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.3K
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...
6.3K
Radical Formation: Homolysis00:54

Radical Formation: Homolysis

4.1K
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.
4.1K
Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

2.3K
The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
2.3K
Radical Formation: Elimination00:51

Radical Formation: Elimination

2.1K
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 with respect...
2.1K

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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Room-temperature Pd/Ag direct arylation enabled by a radical pathway.

Amy L Mayhugh1, Christine K Luscombe2

  • 1Department of Chemistry, University of Washington, Seattle, WA 98195, USA.

Beilstein Journal of Organic Chemistry
|April 8, 2020
PubMed
Summary

Room-temperature direct arylation polymerization (DArP) offers a cost-effective and energy-efficient route to π-conjugated materials. Mechanistic studies reveal these polymerizations are radical-mediated, challenging traditional two-electron mechanisms.

Keywords:
direct arylationindolepalladium radicalvisible light

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Polymer Chemistry

Background:

  • Direct arylation is a valuable synthetic method for π-conjugated materials, bypassing prefunctionalization steps.
  • Improving the sustainability and cost-effectiveness of organic electronic materials production is a key goal.
  • Room-temperature polymerization processes enhance energy and economic efficiencies.

Purpose of the Study:

  • To investigate the mechanism of room-temperature direct arylation between iodobenzene and indole.
  • To determine if the observed mechanism applies to other substrates in direct arylation polymerization (DArP).

Main Methods:

  • Palladium/silver-catalyzed direct arylation polymerization (DArP).
  • Mechanistic studies involving iodobenzene and indole as model substrates.
  • Extension of mechanistic findings to benzo[b]thiophene and pentafluorobenzene.

Main Results:

  • Room-temperature direct arylation, catalyzed by Pd/Ag, proceeds via a radical-mediated pathway.
  • This radical mechanism contrasts with previously proposed two-electron mechanisms for direct arylation.
  • The findings are applicable to a range of substrates, including benzo[b]thiophene and pentafluorobenzene.

Conclusions:

  • Direct arylation polymerization (DArP) at room temperature is a radical process.
  • This discovery challenges existing mechanistic models for direct arylation.
  • The radical mechanism provides new insights for developing efficient and sustainable synthetic routes for organic electronic materials.