Scott Bagley (@bagphos.bsky.social)

#ChemSky As a medicinal chemist I often look at sulfonamides as isosteic replacements for R-CO2H and now thanks to the Willis lab @ Oxford @rhpdcu.bsky.social & Sygnature, you can do that synthetically too! One step sp3-CO2H -> sp3-SONH2 and acces to sulfonamides and sulfonimides #OrgLett asap

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Iron-Catalyzed Decarboxylative Sulfinylation of Alkyl Carboxylic Acids 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. https://pubs.acs.org/doi/10.1021/acs.orglett.5c03100