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Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

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.

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

Electrophilic Addition to Alkynes: Halogenation

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

Preparation of Alkynes: Alkylation Reaction

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Electrophilic Aromatic Substitution: Sulfonation of Benzene

Sulfonation of benzene is a reaction wherein benzene is treated with fuming sulfuric acid at room temperature to produce benzenesulfonic acid. Fuming sulfuric acid is a mixture of sulfur trioxide and concentrated sulfuric acid.

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Updated: Oct 3, 2025

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

Published on: August 19, 2012

Sulfonium Triggered Alkyne-Azide Click Cycloaddition.

Zhanfeng Hou^1,2, Yuena Wang¹, Chuan Wan¹

¹State Key Laboratory of Chemical Oncogenomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China.

Organic Letters

|February 14, 2022

Summary

We developed a novel, copper-free click reaction using alkynyl sulfonium and azide in water. This efficient method is suitable for biological applications due to its mild conditions and biocompatible reagents.

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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry

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Published on: September 8, 2013

Area of Science:

Organic Chemistry
Chemical Biology

Background:

Click chemistry offers efficient molecular ligation but often requires metal catalysts.
Copper-catalyzed azide-alkyne cycloaddition (CuAAC) is widely used but faces limitations in biological systems due to copper toxicity.

Purpose of the Study:

To develop a novel, metal-free click reaction for bioconjugation.
To explore the utility of alkynyl sulfonium compounds in bioorthogonal chemistry.

Main Methods:

A facile Cu-free click reaction between alkynyl sulfonium and azide was developed.
Density Functional Theory (DFT) computations were employed to elucidate the reaction mechanism.
Synthesis and scale-up of sulfonium alkynes were performed.
Biocompatibility of sulfonium alkynes was assessed.
Candidate molecules were prepared and tested in biological applications.

Main Results:

The first Cu-free click reaction between alkynyl sulfonium and azide was achieved under ambient conditions in aqueous media.
DFT calculations revealed that the sulfonium group enhances reactivity by stabilizing the LUMO+1 and influencing the alkyne's charge distribution.
Sulfonium alkynes are easily synthesized, scalable, and generally biocompatible.
Proof-of-concept biological applications demonstrated the potential of this new reaction.

Conclusions:

Alkynyl sulfonium compounds represent a promising new class of reagents for Cu-free click chemistry.
This reaction offers a biocompatible and efficient alternative to traditional click reactions for biological labeling and modification.
The facile synthesis and scalability of sulfonium alkynes facilitate their broader application in chemical biology and drug discovery.