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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
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

1.3K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
1.3K
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

3.2K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
3.2K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

8.0K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
8.0K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.4K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
1.4K
Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation00:43

Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation

2.2K
As shown in Figure 1, under acidic conditions, the β-hydroxy ketone undergoes dehydration via an E1 elimination reaction to form an enone.
2.2K

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Related Experiment Video

Updated: May 2, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

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Repairing the thiol-ene coupling reaction.

Guillaume Povie1, Anh-Tuan Tran, David Bonnaffé

  • 1Universität Bern, Departement für Chemie und Biochemie, Freiestrasse 3, 3012 Bern (Switzerland).

Angewandte Chemie (International Ed. in English)
|March 12, 2014
PubMed
Summary
This summary is machine-generated.

This study introduces a novel method to improve thiol-ene coupling (TEC) reactions involving difficult C-H bonds. By adding triethylborane and catechol, researchers achieved efficient coupling for various sugar derivatives.

Keywords:
allylic compoundsboranesglycosidesradical reactionssynthetic methods

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Area of Science:

  • Organic Chemistry
  • Carbohydrate Chemistry
  • Radical Chemistry

Background:

  • Thiol-ene coupling (TEC) is a versatile reaction for molecular assembly under mild conditions.
  • TEC reactions involving weak allylic and benzylic C-H bonds are often inefficient due to competing hydrogen-atom transfer processes.
  • Existing methods struggle to overcome these competing radical pathways.

Purpose of the Study:

  • To develop a strategy for enhancing the efficiency of thiol-ene coupling reactions involving challenging C-H bonds.
  • To investigate a novel repair mechanism for radical-chain processes in TEC.
  • To demonstrate the applicability of this method to complex carbohydrate structures.

Main Methods:

  • Investigated the mechanism of thiol-ene coupling reactions with allylic and benzylic C-H bonds.
  • Introduced a reaction system employing triethylborane and catechol to repair radical-chain processes.
  • Applied the developed method to a diverse range of anomeric O-allyl sugar derivatives, including mono-, di-, and tetrasaccharides.

Main Results:

  • Identified hydrogen-atom transfer as a key limitation in TEC of allylic/benzylic substrates.
  • Developed a unique repair mechanism using triethylborane and catechol that overcomes competing reactions.
  • Achieved efficient thiol-ene coupling with a broad scope of functionalized and protected sugar derivatives.

Conclusions:

  • The developed triethylborane and catechol system effectively repairs radical-chain processes in thiol-ene coupling.
  • This method significantly improves the efficiency of TEC involving weak C-H bonds, particularly in carbohydrate chemistry.
  • The strategy is broadly applicable to complex carbohydrate synthesis, offering a valuable tool for organic chemists.