The invention of radical reactions: Part XVII. A decarboxylative sulphonylation of carboxylic acids

✍ Scribed by Derek H.R. Barton; Brigitte Lacher; Boguslaw Misterkiewicz; Samir Z. Zard

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 433 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)85895-6

✦ Synopsis

Irradiation with visible light of N-hydraxy-2-thiopyridone esters f in the presence of sulphur dioxidrgave the corresponding th~os~fp~o~otes 4 in good yiefd. These could be converted to s&phones 5 by-treatment with KOH and an alkylating ogent. Alternatively, exposure to sulphuryl chloride followed by a primary or secondary amine afforded sulphonamides 6. The carboxyllc acid function is present in many classes of natural compounds, some of which are of paramount biological importance. These include the amino acids, the bile acids, prostaglandins and leukotrienes, to name but a few. The possibility of manipulating this ubiquitous functional group under mild conditions should therefore open up new vistas in terms of partial syntheses and improved biological activity profiles.