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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Electrophilic Aromatic Substitution: Nitration of Benzene01:20

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The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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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.
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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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Light-promoted aromatic denitrative chlorination.

Tiantian Liang1, Zhen Lyu2, Ye Wang1

  • 1CCNU-uOttawa Joint Research Centre, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, China.

Nature Chemistry
|January 20, 2025
PubMed
Summary
This summary is machine-generated.

A new visible-light-driven reaction enables direct denitrative chlorination of unactivated nitroarenes. This method overcomes the inertness of the carbon-nitro bond, offering a versatile synthetic route for nitro group transformations.

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Synthetic Methodology

Background:

  • Nitroarenes are valuable synthetic precursors, but direct substitution of the nitro group is hindered by the robust CAr-NO2 bond.
  • Existing methods for nitro group transformation often involve multi-step sequences like reduction-diazotization-Sandmeyer reactions or require activated arenes for nucleophilic aromatic substitution.

Purpose of the Study:

  • To develop a general and direct method for denitrative substitution of unactivated nitroarenes.
  • To achieve nitro group transformation via a novel chlorination reaction under visible-light irradiation.

Main Methods:

  • Visible-light-mediated photocatalysis for denitrative chlorination.
  • Utilized chlorine radical for CAr-NO2 bond cleavage and substitution.
  • Density functional theory (DFT) calculations to elucidate the reaction mechanism.

Main Results:

  • A practical denitrative chlorination reaction applicable to a wide range of unactivated nitro(hetero)arenes and nitroalkenes was established.
  • The reaction proceeds efficiently under visible-light irradiation, is air and moisture tolerant, and scalable to decagram quantities.
  • The developed method offers a distinct synthetic approach and mechanistic pathway compared to traditional thermal nucleophilic aromatic substitution reactions.

Conclusions:

  • The developed visible-light-driven denitrative chlorination provides a powerful new tool for transforming nitroarenes.
  • This method simplifies synthetic routes by directly replacing the nitro group with chlorine, bypassing challenging sequential steps.
  • The study expands the synthetic utility of readily available nitroarene starting materials.