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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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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...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.6K
Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

2.6K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
2.6K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.7K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
5.8K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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

5.8K
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...
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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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O2-Mediated Cu-Catalyzed Dehydrogenative Phenothiazination.

Fang Xiao1, Xingben Wang1, Ben Ebel2

  • 1Institute of Organic Chemistry, RWTH Aachen University, 52074 Aachen, Germany.

The Journal of Organic Chemistry
|January 2, 2025
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Summary

A new copper-catalyzed method makes dehydrogenative phenothiazination reactions mild and sustainable. This cost-effective approach uses simple conditions, offering a green alternative for practical coupling chemistry.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry

Background:

  • Dehydrogenative phenothiazination reactions are often perceived as requiring complex conditions.
  • There is a need for milder, more sustainable synthetic methods in organic chemistry.

Purpose of the Study:

  • To demonstrate a facile, cost-effective, and sustainable method for dehydrogenative phenothiazination.
  • To challenge the notion that this reaction requires advanced technologies or catalysts.

Main Methods:

  • Utilized a copper(II) catalyst for the reaction.
  • Conducted the reaction under 1 atm of oxygen at room temperature in methanol.
  • Showcased broad substrate scope and high product yields.

Main Results:

  • Achieved mild and sustainable dehydrogenative phenothiazination.
  • The reaction proceeded efficiently under ambient conditions.
  • Demonstrated broad scope and high yields with a simple Cu(II) catalyst.

Conclusions:

  • Dehydrogenative phenothiazination can be achieved through simple, cost-effective, and sustainable methods.
  • This copper-catalyzed approach represents a practical and green coupling concept.
  • The findings contribute to the advancement of sustainable synthetic chemistry.