Sodium thiosulfate-catalysed synthesis of thioethers from aldehydes or carboxylic acids.

Abstract

This article presents a straightforward and efficient method for the synthesis of thioethers from the reaction of aldehydes or carboxylic acids with thiols, utilizing sodium thiosulfate as a catalyst and N,N-dimethylformamide (DMF) as a solvent. The coupling reactions, facilitated by sodium thiosulfate, lead to the formation of thioethers through the generation of stable thiyl radicals. These metal-free processes are highly valuable for constructing C-S bonds from readily available coupling partners. Various aldehydes and carboxylic acids, including 2-phenylpropionaldehyde, 2-phenylpropanoic acid, phenylacetic acid, 1-naphthaleneacetic acid and 2-furanacetic acid, were successfully employed as coupling partners. Notably, this method was also applied to structurally complex bioactive molecules, including the anti-inflammatory drugs indomethacin and ibuprofen, which contain a carboxylic acid group, successfully affording the corresponding thioethers in acceptable yields. The results demonstrate that sodium thiosulfate is an effective and practical catalyst for these transformations, offering a mild and environmentally benign strategy for C-S bond formation with broad substrate scope.