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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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Phase II Reactions: Sulfation and Conjugation with α-Amino Acids01:19

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Sulfation and α-amino acid conjugation are two critical biotransformation reactions in drug metabolism. Sulfation, a phase II biotransformation reaction, involves adding a polar sulfate group to a drug, enhancing its water solubility and promoting excretion. This process can either co-occur with or occur independently of glucuronidation. Nonmicrosomal sulfotransferase enzymes catalyze the process. The reaction involves 3'-phosphoadenosine-5'-phosphosulfate or PAPS coenzyme...
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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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SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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¹H NMR: Long-Range Coupling01:27

¹H NMR: Long-Range Coupling

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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)01:20

Spin–Spin Coupling: Two-Bond Coupling (Geminal Coupling)

1.5K
Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
The central atom need not be NMR-active because its electrons are affected by the electron polarization of the spin-active atoms. However, spin information is transmitted less effectively than in one-bond coupling, and 2J values are usually weaker than 1J values. The energy of...
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Sequential C-S and S-N Coupling Approach to Sulfonamides.

Kai Chen1, Wei Chen1, Bing Han1

  • 1Department of Chemistry, Zhejiang University, 38 Zheda Road, Hangzhou 310027, China.

Organic Letters
|February 20, 2020
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Summary

A novel one-pot reaction synthesizes diverse sulfonamides from nitroarenes and boronic acids using potassium pyrosulfite. This metal-free method efficiently creates C-S and S-N bonds for various functionalized sulfonamides.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Sulfonamides are crucial in pharmaceuticals and materials science.
  • Efficient and metal-free synthetic routes are highly desirable.

Purpose of the Study:

  • To develop a novel, efficient, and metal-free method for sulfonamide synthesis.
  • To explore a one-pot, three-component reaction for broad applicability.

Main Methods:

  • A one-pot, three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite.
  • Sequential C-S and S-N coupling strategies were employed.

Main Results:

  • A broad range of sulfonamides were synthesized with good to excellent yields.
  • The reaction is metal-free and tolerates various functional groups.
  • Diverse sulfonamides bearing reactive functional groups were obtained.

Conclusions:

  • The developed method provides an efficient and versatile route to sulfonamides.
  • This metal-free approach offers a sustainable alternative for sulfonamide synthesis.