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Related Concept Videos

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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Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Preparation of Nitriles01:12

Preparation of Nitriles

2.1K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.1K
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,...
2.1K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

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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.
6.0K
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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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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Nitro-sulfinate Reductive Coupling to Access (Hetero)aryl Sulfonamides.

Sandra E Gatarz1, Oliver M Griffiths1, Henrique A Esteves1

  • 1Yusuf Hamied Department of Chemistry, University of Cambridge, Cambridge CB2 1EW, U.K.

The Journal of Organic Chemistry
|January 19, 2024
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Researchers developed a new method for synthesizing sulfonamides using reductive coupling of aryl sulfinates and nitroarenes. This ultrasound-assisted approach offers an efficient route to diverse sulfonamide compounds.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Sulfonamides are crucial pharmacophores found in numerous drugs.
  • Efficient synthetic routes for diverse sulfonamide scaffolds are highly sought after.

Purpose of the Study:

  • To report a novel method for synthesizing (hetero)aryl sulfonamides.
  • To explore reductive coupling of aryl sulfinates and nitroarenes.

Main Methods:

  • Utilized reductive coupling of aryl sulfinates and nitroarenes.
  • Employed sodium bisulfite as a reducing agent, with or without tin(II) chloride.
  • Incorporated an ultrasound bath to enhance reaction homogeneity and mixing.
  • Investigated various reaction conditions in dimethyl sulfoxide (DMSO).

Main Results:

  • Successfully synthesized a range of (hetero)aryl sulfonamides with diverse functional groups.
  • Established the mechanism of the transformation, proposing nitrosoarene intermediates.
  • Confirmed nitrosoarene intermediate formation via an independent molecular coupling strategy.

Conclusions:

  • The developed method provides an efficient pathway to (hetero)aryl sulfonamides.
  • The study elucidates the reaction mechanism, highlighting the role of nitrosoarene intermediates.
  • This work contributes a valuable synthetic tool for medicinal and organic chemistry.