Installation of -SO₂F groups onto primary amides

Area of Science:

• Organic Chemistry
• Medicinal Chemistry
• Chemical Biology

Background:

• Sulfur(VI) fluoride exchange (SuFEx) click chemistry is a powerful tool for molecular construction.
• Primary amides are versatile building blocks in organic synthesis.
• Developing new methods for functionalizing amides is crucial for drug discovery.

Purpose of the Study:

• To develop a novel protocol for installing sulfonyl fluoride moieties onto primary amides.
• To expand the scope of SuFEx click chemistry.
• To generate novel molecules with potential pharmaceutical applications.

Main Methods:

• Reaction of primary amides with sulfuryl fluoride (SO₂F₂) under specific conditions.
• Purification and characterization of the resulting sulfonyl fluoride products.
• Exploration of the utility of the products in SuFEx click chemistry.

Main Results:

• A robust protocol for SO₂F₂-mediated sulfonylation of primary amides was established.
• The generated molecules possess both amide and sulfonyl fluoride functionalities.
• The products are suitable for further derivatization via SuFEx click chemistry.

Conclusions:

• The developed method provides a new and efficient route to sulfonyl fluorides from primary amides.
• This work expands the toolkit for SuFEx click chemistry.
• The resulting compounds hold promise for the discovery of new therapeutics.