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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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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.
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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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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.8K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
1.8K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.2K
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...
5.2K
Conversion of Alcohols to Alkyl Halides02:48

Conversion of Alcohols to Alkyl Halides

7.3K
This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...
7.3K
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.3K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.3K

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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Electroreductive Desulfurative Transformations with Thioethers as Alkyl Radical Precursors.

Julius Kuzmin1, Johannes Röckl1, Nils Schwarz1

  • 1Department of Chemistry, KTH Royal Institute of Technology, 10044, Stockholm, Sweden.

Angewandte Chemie (International Ed. in English)
|June 21, 2023
PubMed
Summary

Thioethers can now be efficiently used as precursors for alkyl radicals in electroreductive transformations. This research unlocks new synthetic methods for desulfurative reactions, offering mild conditions and broad functional group tolerance.

Keywords:
C−C CouplingDesulfurizationElectrosynthesisRadical ReactionsThioether

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Methodology

Background:

  • Thioethers are common in natural and synthetic compounds but are underutilized in desulfurative transformations.
  • Developing new synthetic methods is crucial to harness the potential of thioethers.
  • Electrochemistry offers mild conditions and enables novel reactivity and selectivity.

Purpose of the Study:

  • To demonstrate the efficient use of aryl alkyl thioethers as alkyl radical precursors in electroreductive reactions.
  • To explore new desulfurative transformations, including hydrodesulfurization, C-C bond formation, and carboxylation.
  • To elucidate the mechanistic details of these electroreductive transformations.

Main Methods:

  • Electrochemical reduction of aryl alkyl thioethers.
  • Mechanistic studies to understand the C(sp3)-S bond cleavage selectivity.
  • Application of the developed methods to hydrodesulfurization, Giese-type cross-coupling, and electrocarboxylation.

Main Results:

  • Complete selectivity for C(sp3)-S bond cleavage was achieved, distinct from transition metal-catalyzed routes.
  • A hydrodesulfurization protocol with broad functional group tolerance was developed.
  • The first examples of desulfurative C(sp3)-C(sp3) bond formation and thioether-based electrocarboxylation were reported.

Conclusions:

  • Aryl alkyl thioethers are effective precursors for alkyl radicals in electroreductive transformations.
  • The developed methods provide novel and efficient routes for desulfurative synthesis.
  • Thioethers show significant potential, outcompeting sulfones in one-electron desulfurative pathways.