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            <funder>L.N. thanks IDEX Paris-Saclay, “ADI 2022” ANR-11-IDEX-0003-02 and Fondazione Cariplo (Photo and Mechano-Chemistry for the Upgrading of Agro- and Sea-food Waste to advanced polymers and nanocarbon materials, CUBWAM, project 2021–0751) for the doctoral fellowships. E. M.-I., L.N., E.D., N.T., and G.M. thanks ANR-24-CE07-4322 and CNRS for the financial supports. L. D. and S.P. are grateful to the Italian Ministry for Universities and Research, Next-GenerationEU - National Recovery and Resilience Plan (NRRP), Project no. P2022HSF3R – PRIN 2022 PNRR - CUP F53D23008990001 “Xylonite: the new season of Xylochemistry”. S.P. and M.F. are grateful to Ministero dell’Università e della Ricerca (MUR) and the University of Pavia through the program “Dipartimenti di Eccellenza 2023–2027.</funder>
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              <p>We present a photocatalyst-free, visible-light-mediated Truce-Smiles rearrangement (TSR) for the selective difunctionalization of olefins by exploiting photoactivatable arylazo sulfones as sulfonyl radical precursors. This method efficiently affords β-sulfonyl-α-arylpropamides in high yields with excellent stereoselectivity. Furthermore, by incorporating a readily available chiral amino acid auxiliary (α-tert-butyl-leucine), we successfully developed a stereoselective variant of the TSR reaction, delivering optically enriched α-arylpropamides with excellent diastereoselectivity (up to 20:1 dr). DFT calculations provided detailed insight into the key factors governing reactivity and selectivity, particularly the contrasting behaviors of N-alkyl and N-aryl acrylamides. Overall, this work provides a sustainable and practical method for constructing sulfonylated aryl compounds under mild and catalyst-free conditions.</p>
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