Mechanochemical-Assisted Decarboxylative Sulfonylation of α,β-Unsaturated Carboxylic Acids with Sodium Sulfinate Salts

Developing a green and efficient method for synthesizing vinyl sulfones is challenging and highly desirable. We hereby report a green, sustainable, and unprecedented mechanochemical-assisted approach for the decarboxylative sulfonylation of α,β-unsaturated carboxylic acids with sodium sulfinates using only potassium iodide (50 mol%) as an activator under water-assisted grinding conditions. A library of alkyl and aryl vinyl sulfone derivatives was synthesized successfully up to 92% yield with excellent functional group compatibility under a short reaction time. This sulfonylation strategy is well tolerated by aryl α,β-unsaturated carboxylic acids, and alkyl and aryl sodium sulfinate salts. The advantages of this strategy are (i) metal catalyst-, base-, oxidant-, and solvent-free, (ii) operationally simple with a short reaction time, (iii) excellent effective mass yield, atom economy, E-factor, and EcoScale score. The practicality of this method is also demonstrated in the gram-scale synthesis of vinyl sulfones.