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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.9K
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.
6.9K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.2K
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.
5.2K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.9K
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...
1.9K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.5K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.5K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

3.3K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
3.3K
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

5.2K
Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
5.2K

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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Paired Electrolysis Enabled Ni-Catalyzed Unconventional Cascade Reductive Thiolation Using Sulfinates.

Jun-Chen Kang1, Zi-Hao Li1, Chao Chen1

  • 1School of Chemistry and Chemical Engineering, Key Laboratory for Thin Film and Microfabrication of Ministry of Education & Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University, Shanghai 200240, P. R. China.

The Journal of Organic Chemistry
|October 11, 2021
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Summary

This study introduces a nickel-catalyzed method for synthesizing thioethers from aryl halides and sulfinates using paired electrolysis. The novel approach enables cascade reactions at the electrode interface under mild conditions.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Catalysis

Background:

  • Thioethers are important organic compounds with diverse applications.
  • Developing efficient and mild methods for thioether synthesis is crucial.
  • Electrochemical methods offer sustainable alternatives in organic synthesis.

Purpose of the Study:

  • To develop a novel nickel-catalyzed cascade reductive thiolation of aryl halides.
  • To utilize sulfinates as a sulfur source for thioether synthesis.
  • To explore the mechanism and potential of paired electrolysis in driving cascade reactions.

Main Methods:

  • Nickel-catalyzed reductive thiolation reaction.
  • Paired electrolysis technique.
  • Synthesis of various thioethers from aryl halides and sulfinates.

Main Results:

  • Successful synthesis of diverse thioethers under mild conditions.
  • Demonstration of a cascade chemical step occurring at the electrode interface.
  • Identification of a novel reaction pathway enabled by paired electrolysis.

Conclusions:

  • The reported protocol provides an efficient route to thioethers.
  • Paired electrolysis can significantly alter reaction pathways and enable cascade processes.
  • This work opens avenues for discovering new cascade reactions with unique reactivity.