Abstract
Catalyst-free reactions employing renewable resources are needed for sustainable development. For example, biologically important β-keto sulfones have been recently synthesized by decarboxylative-coupling reaction between arylpropiolic acids and sulfonic acid derivatives. Nonetheless, existing protocols involve harsh conditions, complicated work-up, and the use of metal catalysts and extra oxidants. To address these shortcomings, we propose here catalyst-free decarboxylative oxysulfonylations of arylpropiolic acids employing air as a green oxidant. Arylpropiolic acids and sodium sulfinates are mixed in the hexafluoroisopropanol solvent under an aerobic atmosphere at room temperature. The results show that β-keto sulfones are formed in 60–97% yields. The products are purified by simple recrystallization. This method is also used to the direct synthesis of bioactive agents and the late-stage functionalization of an estrone derivative.
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Acknowledgements
The author acknowledges generous financial support from the Scientific and Technological Innovation Project of China Academy of Chinese Medical Sciences CI2021A05102, the National Natural Science Foundation of China (21702235, 81841001), and the Fundamental Research Funds for the Central Public Welfare Research Institutes (ZZ13-YQ-098, ZZ14-FL-010, ZZ15-ND-10). We thank Mr. Timothy Barnes at Auburn University for the help of preparing the manuscript.
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Chen, X., Chang, X., Zhang, S. et al. Air-triggered, catalyst-free decarboxylative oxysulfonylation of arylpropiolic acids with sodium sulfinates. Environ Chem Lett 20, 2773–2779 (2022). https://doi.org/10.1007/s10311-022-01440-x
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DOI: https://doi.org/10.1007/s10311-022-01440-x