Article Dans Une Revue Journal of Organic Chemistry Année : 2024

Investigation of UV Light-Promoted Synthesis of α-Sulfonyl Amides from N -Sulfonyl Ynamides

Résumé

UV Light-promoted synthesis of α-sulfonyl amides from N-sulfonyl ynamides without any additives is reported. The reaction proceeds through a radical chain mechanism involving the photo-induced cleavage of the nitrogen-sulfur bond, addition of electrophilic sulfonyl radical to the triple bond of the ynamide followed by beta-fragmentation of the sulfonyl group leading to a ketenimine hydrated upon work-up. This highly efficient rearrangement leads, after acidic treatment, to a wide range of α-sulfonyl amides in high yields.

Domaines

Chimie organique
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Dates et versions

hal-04643937 , version 1 (10-07-2024)

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Aurélien Galibert-Guijarro, Jérémy Tronc, Dominique Mouysset, Didier Siri, Stéphane Gastaldi, et al.. Investigation of UV Light-Promoted Synthesis of α-Sulfonyl Amides from N -Sulfonyl Ynamides. Journal of Organic Chemistry, 2024, 89 (13), pp.9695-9699. ⟨10.1021/acs.joc.4c01013⟩. ⟨hal-04643937⟩
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