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Related Concept Videos

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.2K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

3.1K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.1K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.2K
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...
5.2K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.5K
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...
8.5K
Halogenation of Alkenes02:46

Halogenation of Alkenes

16.2K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
16.2K

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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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Meerwein-type Bromoarylation with Arylthianthrenium Salts.

Yuan Cai1, Tobias Ritter1

  • 1Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr, Germany.

Angewandte Chemie (International Ed. in English)
|September 7, 2022
PubMed
Summary

This study introduces a new method for attaching aryl groups to alkenes using photocatalysis and arylthianthrenium salts. This approach enables the late-stage functionalization of complex biomolecules for drug discovery.

Keywords:
Arylthianthrenium SaltsBromoarylation of AlkenesLate-Stage FunctionalizationMeerwein Arylation

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Medicinal Chemistry

Background:

  • Aryl coupling reactions are crucial for synthesizing complex organic molecules.
  • Late-stage functionalization of biomolecules remains a significant challenge in drug discovery.
  • Existing aryl coupling methods often lack efficiency or broad applicability for complex substrates.

Purpose of the Study:

  • To develop a novel photocatalyzed Meerwein-type bromoarylation protocol.
  • To utilize stable arylthianthrenium salts for efficient C-H functionalization.
  • To enable the late-stage modification of diverse biomolecules.

Main Methods:

  • Photocatalyzed Meerwein-type bromoarylation using arylthianthrenium salts.
  • Site-selective C-H thianthrenation for precursor synthesis.
  • Application to late-stage functionalization of various biomolecules.

Main Results:

  • Successful bromoarylation of alkenes with arylthianthrenium salts under photocatalysis.
  • Demonstration of late-stage functionalization on challenging biomolecular scaffolds.
  • Introduction of halogens for subsequent diverse chemical transformations.

Conclusions:

  • The developed protocol offers a versatile and efficient route for arylating alkenes.
  • This method expands the toolkit for late-stage functionalization of complex molecules.
  • The ability to introduce halogens facilitates the synthesis of biologically relevant compounds.