A rapid access to aliphatic sulfonyl fluorides.

Area of Science:

• Organic Chemistry
• Chemical Biology
• Medicinal Chemistry

Background:

• Growing interest in sulfonyl fluorides as reactive probes in chemical biology and molecular pharmacology.
• Need for efficient synthetic methods to expand the availability of sulfonyl fluoride compounds.

Purpose of the Study:

• To develop a facile and general synthetic approach for aliphatic sulfonyl fluorides.
• To enable rapid diversification of sulfonyl fluoride-containing molecules for various applications.

Main Methods:

• Visible-light-mediated decarboxylative fluorosulfonylethylation of carboxylic acids.
• Utilizing abundant carboxylic acid feedstocks, including primary, secondary, and tertiary acids.
• Application to natural products such as amino acids, peptides, and drugs.

Main Results:

• Successful synthesis of diverse aliphatic sulfonyl fluorides.
• Demonstrated applicability to a wide range of alkyl carboxylic acids.
• Showcased modification of biologically relevant molecules like amino acids, peptides, and drugs.
• Enabled further diversification into pharmaceutically important motifs like sultams, sulfonates, and sulfonamides.

Conclusions:

• The developed method provides a rapid, metal-free route to sulfonyl fluorides.
• This approach significantly expands the toolkit for synthesizing sulfonyl fluoride derivatives.
• The method facilitates the creation of diverse compound libraries for drug discovery and chemical biology research.