Air-triggered, catalyst-free decarboxylative oxysulfonylation of arylpropiolic acids with sodium sulfinates

• Published in: Environmental chemistry letters 2022-10, Vol.20 (5), p.2773-2779
• Main Authors: Chen, Xingyu, Chang, Xiaoqiang, Zhang, Shuaichen, Lu, Sixian, Yang, Lan, Sun, Peng
• Format: Article
• Language: English
• Subjects: Acids; Analytical Chemistry; By products; Carbon; Catalysts; Chemical synthesis; Chemistry; Earth and Environmental Science; Ecotoxicology; Environment; Environmental Chemistry; Estrone; Geochemistry; Metals; Natural products; Original Paper; Oxidants; Oxidizing agents; Pollution; Recrystallization; Renewable resources; Room temperature; Sodium; Sulfones; Sulfonic acid; Sustainable development; Sustainable yield
• ISSN: 1610-3653; 1610-3661
• DOI: 10.1007/s10311-022-01440-x

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.