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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

3.0K
In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
3.0K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.1K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

4.5K
Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.0K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
12.0K
Catalysis02:50

Catalysis

26.9K
The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Gold catalysis in quinoline synthesis.

Ximei Zhao1, Guanghui Wang1, A Stephen K Hashmi2

  • 1School of Chemistry and Materials Science, Ludong University, Yantai 264025, China. wangguanghui@ldu.edu.cn.

Chemical Communications (Cambridge, England)
|June 21, 2024
PubMed
Summary

Gold catalysis enables efficient synthesis of quinolines, vital N-heterocyclic compounds for medicinal chemistry. This review highlights key gold-catalyzed reactions and mechanisms for constructing these important molecules.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Quinolines are crucial N-heterocyclic aromatic compounds with significant biological and pharmaceutical applications.
  • Efficient synthesis of quinolines is essential for medicinal chemistry and drug discovery.
  • Gold-catalyzed reactions have emerged as powerful tools for quinoline synthesis.

Purpose of the Study:

  • To provide a comprehensive overview of gold-catalyzed methodologies for quinoline synthesis.
  • To summarize recent advancements in reaction development and mechanistic understanding.
  • To highlight the versatility of gold catalysis in constructing diverse quinoline scaffolds.

Main Methods:

  • Review of literature on gold-catalyzed intermolecular annulation reactions.
  • Analysis of gold-catalyzed intramolecular cyclization reactions.
  • Discussion of reaction mechanisms and synthetic strategies.

Main Results:

  • Detailed exploration of various gold-catalyzed annulations (e.g., aniline derivatives with carbonyls/alkynes, anthranils with alkynes, A3-coupling).
  • Coverage of intramolecular cyclizations involving azide-tethered alkynes, 1,2-diphenylethynes, and 2-ethynyl N-aryl indoles.
  • Summary of typical achievements and plausible reaction pathways.

Conclusions:

  • Gold catalysis offers efficient and versatile routes to synthetically valuable quinolines.
  • Understanding reaction mechanisms is key to further developing gold-catalyzed quinoline synthesis.
  • This review consolidates current knowledge, paving the way for future innovations in the field.