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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.9K
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.
7.9K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.9K
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.
5.9K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

4.3K
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...
4.3K
Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

4.1K
Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
4.1K
Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents01:13

Preparation of Carboxylic Acids: Carboxylation of Grignard Reagents

6.3K
Carboxylic acids can be prepared by the carboxylation of Grignard reagents (RMgX). This method is convenient for converting alkyl (primary, secondary or tertiary), vinyl, benzyl, and aryl halides to carboxylic acids with one additional carbon than the starting RMgX.
6.3K
α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

4.3K
Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the...
4.3K

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Related Experiment Video

Updated: Mar 19, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

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

Published on: April 9, 2018

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Aerobic copper-catalyzed decarboxylative thiolation.

Minghao Li1, Jessica M Hoover1

  • 1C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia, USA. Jessica.Hoover@mail.wvu.edu.

Chemical Communications (Cambridge, England)
|June 24, 2016
PubMed
Summary
This summary is machine-generated.

A new copper-catalyzed reaction enables decarboxylative thiolation of aromatic carboxylic acids using oxygen. This method efficiently produces aryl sulfides from various substrates, offering a greener synthetic route.

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

Last Updated: Mar 19, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Decarboxylative thiolation is a valuable transformation for C-S bond formation.
  • Existing methods often require harsh conditions or stoichiometric oxidants.

Purpose of the Study:

  • To develop a novel copper-catalyzed decarboxylative thiolation reaction.
  • To utilize molecular oxygen as a sustainable oxidant.

Main Methods:

  • Copper catalysis
  • Decarboxylative coupling
  • Oxidation with molecular oxygen
  • Substrate scope evaluation with various aromatic and heteroaromatic carboxylic acids

Main Results:

  • Efficient synthesis of aryl sulfides from diverse carboxylic acids.
  • Moderate to excellent yields achieved.
  • Successful application to electron-deficient substrates like 2-nitrobenzoic acids and pentafluorobenzoic acid.

Conclusions:

  • A practical and efficient copper-catalyzed decarboxylative thiolation protocol was established.
  • The method offers a sustainable approach using molecular oxygen.
  • Provides access to valuable aryl sulfide compounds.