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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.7K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
6.7K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.1K
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.
5.1K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.8K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.8K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.4K
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...
5.4K
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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

3.2K
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...
3.2K
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

6.4K
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.
6.4K

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Related Experiment Video

Updated: Sep 16, 2025

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

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Thiol-thiol cross-clicking using bromo-ynone reagents.

Marvin Nicque1, Jan H Meffert2, Diederick Maes1

  • 1Organic Synthesis Group, Department of Organic and Macromolecular Chemistry, Faculty of Sciences, Ghent University, Ghent, Belgium.

Nature Communications
|July 10, 2025
PubMed
Summary

This study introduces bromo-ynones, novel reagents for selective thiol-click reactions. These reagents enable efficient, one-pot synthesis of heterodimers from two distinct thiols in aqueous media.

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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Area of Science:

  • Chemical Biology
  • Organic Synthesis
  • Bioconjugation Chemistry

Background:

  • Thiols are versatile functional groups widely used in click reactions and bioconjugation.
  • Direct cross-coupling of thiols offers a biomimetic approach but typically yields statistical mixtures.

Purpose of the Study:

  • To develop a novel method for the selective, one-pot cross-clicking of two distinct thiols.
  • To introduce a new class of reagents that facilitate stepwise thiol addition.

Main Methods:

  • Introduction of bromo-ynones as thiol-click reagents.
  • Utilizing kinetic differentiation for sequential thiol addition in a one-pot procedure.
  • Demonstration in aqueous media without intermediate purification.

Main Results:

  • Bromo-ynones enable stepwise one-pot cross-clicking of two different thiols.
  • Synthesis of various cross-coupled thiols, including small molecules, peptides, and proteins.
  • Formation of robust adducts, including protein-protein heterodimers, stable under physiological conditions.

Conclusions:

  • Bromo-ynones provide a robust and efficient strategy for selective thiol-thiol cross-coupling.
  • This method overcomes limitations of statistical thiol coupling, enabling precise biomolecular construction.
  • The resulting adducts offer stability and versatility for various applications.