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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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Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...

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Updated: Oct 14, 2025

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB

Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB

Published on: June 28, 2011

Accelerated SuFEx Click Chemistry For Modular Synthesis.

Christopher J Smedley¹, Joshua A Homer², Timothy L Gialelis¹

¹L. I. M. S., Science Dr., Bundoora, Melbourne, VIC, 3086, Australia.

Angewandte Chemie (International Ed. in English)

|November 10, 2021

Summary

This summary is machine-generated.

Accelerated SuFEx click chemistry (ASCC) uses Barton

Keywords:

SuFEx click chemistry guanidines organocatalysis synthetic methods

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Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB

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Area of Science:

Organic Chemistry
Chemical Synthesis

Background:

Sulfur(VI) fluoride exchange (SuFEx) click chemistry enables selective and modular synthesis of functional molecules.
Classical SuFEx reactions can require high catalyst loadings and long reaction times.

Purpose of the Study:

To develop an accelerated SuFEx click chemistry (ASCC) method for efficient and catalytic coupling.
To improve SuFEx reaction efficiency using novel catalysts and additives.

Main Methods:

Development of accelerated SuFEx click chemistry (ASCC).
Utilized Barton's hindered guanidine base (BTMG) as a catalyst.
Synergistic use of hexamethyldisilazane (HMDS) as a silicon additive.

Main Results:

ASCC enables rapid, single-step formation of stable S-O linkages within minutes.
BTMG and HMDS combination allows for low catalyst loadings (1.0 mol%).
Demonstrated efficient coupling of aryl and alkyl alcohols with SuFExable hubs.

Conclusions:

ASCC is a scalable, safe, and practical method for modular synthesis.
This accelerated approach expands accessible SuFEx products.
ASCC holds significant potential for organic synthesis, medicinal chemistry, and materials science.