Work

Iron-Catalyzed Decarboxylative Sulfinylation of Alkyl Carboxylic Acids

Year: 2025

Type: article

Abstract: Sulfinamides, sulfonamides, and sulfonimidamides are valuable motifs in medicinal chemistry, yet methods to synthesize alkyl variants from simple, readily available feedstocks remain scarce. In this report, we detail the synthesis of these three distinct sulfur functional groups, using readily available and structurally diverse alkyl carboxylic acids as the starting materials. The method harnesses alkyl radical generation from carboxylic acids using commercial iron salts and visible light irradiation, in combination with commercial sulfinylamine reagents, to deliver alkyl sulfinamide products. The method is operationally simple and scalable, exhibits broad functional group tolerance, and is translatable to continuous-flow synthesis. Furthermore, it facilitates late-stage diversification of complex molecules, highlighting its potential utility in medicinal chemistry applications.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c03100

Authors: Matthew Southern, Christopher Pearce, Michael C. Willis

Institution: University of Oxford

Language: English

Topic: Sulfur-Based Synthesis Techniques

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Royal Commission for the Exhibition of 1851