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Related Concept Videos

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...
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Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

1.7K
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...
1.7K
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 Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.1K
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...
2.1K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.2K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.2K
Radical Reactivity: Concentration Effects01:20

Radical Reactivity: Concentration Effects

1.5K
In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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An Efficient C-Si/C-H Cross-Coupling Reaction Enabled by a Radical Pathway.

Chunchun Mi1, Bei-Bei Zhang2, Guanghao Zhang1

  • 1College of Materials Science and Opto-Electronic Technology & Center of Materials Science and Optoelectronics Engineering & CAS Center for Excellence in Topological Quantum Computation & CAS Key Laboratory of Vacuum Physics, University of Chinese Academy of Sciences, Beijing, 100049, P. R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 11, 2024
PubMed
Summary

This study introduces a novel copper-catalyzed method for cross-coupling aryl(trialkyl)silanes, overcoming the inert C-Si bond challenge. This efficient reaction provides a new route to synthesize biaryls using a radical mechanism.

Keywords:
aryl sulfonium saltsbiarylcopper-catalyzed cross-couplingorganosilanesradical reaction

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cross-coupling reactions are vital for synthesizing biaryls, but coupling aryl(trialkyl)silanes remains challenging due to the inert carbon-silicon bond.
  • Existing methods often require harsh conditions or lack broad applicability, necessitating the development of milder, more efficient strategies.
  • Aryl(trialkyl)silanes offer an environmentally benign alternative for cross-coupling due to silicon's low toxicity and the reaction's regioselectivity.

Purpose of the Study:

  • To develop a novel copper-catalyzed cross-coupling method for aryl(trialkyl)silanes and aryl compounds.
  • To establish an efficient and regioselective synthetic strategy for biaryl synthesis via a radical pathway.
  • To investigate the reaction mechanism, including the roles of the copper catalyst and cesium fluoride (CsF).

Main Methods:

  • Copper-catalyzed cross-coupling reaction utilizing aryl(trialkyl)silanes and aryl sulfonium salts.
  • Employing a radical mechanism initiated by the copper catalyst and CsF.
  • Conducting experimental and theoretical mechanistic studies to elucidate the reaction pathway.

Main Results:

  • Efficient cross-coupling of aryl(trialkyl)silanes achieved under mild conditions.
  • Broad substrate scope demonstrated, yielding various biaryl compounds.
  • Successful application in synthesizing unsymmetrical fluorescence probes and late-stage functionalization of drug molecules.

Conclusions:

  • A novel and efficient copper-catalyzed radical cross-coupling method for aryl(trialkyl)silanes has been developed.
  • The reaction proceeds efficiently with aryl sulfonium salts as limiting reagents, offering a versatile synthetic strategy for biaryls.
  • Mechanistic studies confirmed a radical pathway involving critical roles for the copper catalyst and CsF in radical generation and desilylation.