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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
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Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

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

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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...
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Amines to Sulfonamides: The Hinsberg Test01:23

Amines to Sulfonamides: The Hinsberg Test

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The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
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Electrophilic Aromatic Substitution: Sulfonation of Benzene01:22

Electrophilic Aromatic Substitution: Sulfonation of Benzene

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Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.
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Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
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Site-Selective C-H Functionalization-Sulfination Sequence to Access Aryl Sulfonamides.

Eva Maria Alvarez1, Matthew B Plutschack1, Florian Berger1

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

Organic Letters
|April 8, 2020
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Summary

This study introduces a new method for creating aryl sulfonamides using aryl sulfonium salts. This efficient process utilizes a palladium catalyst and sodium hydroxymethylsulfinate (Rongalite) for site-selective C-H sulfination.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Aryl sulfinates are key precursors for sulfonyl-derived arenes, prevalent in pharmaceuticals and agrochemicals.
  • Developing efficient and site-selective methods for introducing sulfonyl groups is crucial for synthesizing these valuable compounds.

Purpose of the Study:

  • To report a novel two-step C-H sulfination sequence for accessing aryl sulfonamides.
  • To develop an operationally simple, one-pot palladium-catalyzed protocol for sulfonyl group introduction.

Main Methods:

  • Utilizing aryl sulfonium salts for site-selective C-H sulfination.
  • Employing a palladium-catalyzed one-pot reaction with sodium hydroxymethylsulfinate (Rongalite) as the SO22- source.
  • Combining site-selective aromatic thianthrenation with the sulfination sequence.

Main Results:

  • Successful synthesis of aryl sulfonamides via a two-step C-H sulfination sequence.
  • Demonstration of an efficient one-pot palladium-catalyzed protocol for sulfonyl group introduction.
  • Generation of a hydroxymethyl sulfone intermediate usable as a synthetic handle for diverse sulfonyl compounds.

Conclusions:

  • The developed method provides a facile route to aryl sulfonamides and other sulfonyl-containing compounds.
  • The one-pot protocol offers operational simplicity and efficiency in synthesizing valuable chemical motifs.
  • The hydroxymethyl sulfone intermediate expands the utility of this catalytic process for broader applications in organic synthesis.