3-Sulfonyl Indoles via Gold-or Silver-Catalyzed Cyclization -1,3-Sulfonyl Migration Sequences under Visible Light Irradiation - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue ACS Organic & Inorganic Au Année : 2022

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

Chimie
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Dates et versions

hal-04293443 , version 1 (18-11-2023)

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Fen Zhao, Wided Hagui, María Ballarín-Marión, Cyril Ollivier, Virginie Mouriès-Mansuy, et al.. 3-Sulfonyl Indoles via Gold-or Silver-Catalyzed Cyclization -1,3-Sulfonyl Migration Sequences under Visible Light Irradiation. ACS Organic & Inorganic Au, 2022, 3 (1), pp.19-26. ⟨10.1021/acsorginorgau.2c00034⟩. ⟨hal-04293443⟩
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