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

Autor:	Galibert-Guijarro A; Aix Marseille Univ, CNRS, ICR, Marseille, 13013, France., Tronc J; Aix Marseille Univ, CNRS, ICR, Marseille, 13013, France., Mouysset D; Aix Marseille Univ, CNRS, ICR, Marseille, 13013, France., Siri D; Aix Marseille Univ, CNRS, ICR, Marseille, 13013, France., Gastaldi S; Aix Marseille Univ, CNRS, ICR, Marseille, 13013, France., Bertrand MP; Aix Marseille Univ, CNRS, ICR, Marseille, 13013, France., Feray L; Aix Marseille Univ, CNRS, ICR, Marseille, 13013, France.
Jazyk:	angličtina
Zdroj:	The Journal of organic chemistry [J Org Chem] 2024 Jul 05; Vol. 89 (13), pp. 9695-9699. Date of Electronic Publication: 2024 Jun 18.
DOI:	10.1021/acs.joc.4c01013
Abstrakt:	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 photoinduced cleavage of the nitrogen-sulfur bond and addition of an electrophilic sulfonyl radical to the triple bond of the ynamide followed by β-fragmentation of the sulfonyl group leading to a ketenimine hydrated upon workup. This highly efficient rearrangement leads, after acidic treatment, to a wide range of α-sulfonyl amides in high yields.
Databáze:	MEDLINE
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