3-Sulfonyl Indoles via Gold-or Silver-Catalyzed Cyclization -1,3-Sulfonyl Migration Sequences under Visible Light Irradiation
Résumé
A pathway for the synthesis of 3-sulfonyl indoles has been devised. Upon blue LED irradiation, in the presence of a gold(I) or a silver(I) salt, ortho-alkynyl N-sulfonyl precursors readily undergo a 5-endo-dig cyclization concomitant with a 1,3sulfonyl migration. While the gold-catalyzed reaction takes place in photocatalyst-free conditions, an iridium photocatalyst (Ir[dF(CF3)ppy]2(dtbbpy)PF6) is necessary with silver catalysis. Mechanistic studies featuring the generation of a sulfonyl radical support this dichotomy.
Domaines
ChimieOrigine | Fichiers produits par l'(les) auteur(s) |
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