Article Dans Une Revue Organic Chemistry Frontiers Année : 2024

Visible light-mediated gold-catalyzed alkynylative cyclization of allenoates with iodoalkynes for the synthesis of β-alkynyl-γbutenolides

Résumé

A method for the tandem cyclization/alkynylation of allenoates with iodoalkynes via gold catalysis under light irradiation is described. This transformation features a broad substrate scope, good functional group tolerance, and compatibility with heterocyclic substrates. The reaction proceeds smoothly at room temperature by using cheap, readily available acriflavine (ACF) as a photocatalyst, and offers β-alkynyl-γ-butenolides derivatives in moderate to good yields. Initial mechanistic studies suggest that a vinylgold(I) complex acts as a key intermediate, which would undergo photosensitization from the ACF singlet excited state. The corresponding energy transfer would promote the oxidative addition of the iodoalkyne partner to deliver C(sp 2 )-C(sp) coupling products after reductive elimination.

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Chimie
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vendredi 7 mars 2025
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Dates et versions

hal-04797045 , version 1 (22-11-2024)

Identifiants

Citer

Yuanhao He, Yu Zhong, Maria Ballarin Marion, Jorge C Herrera, Wanping Ma, et al.. Visible light-mediated gold-catalyzed alkynylative cyclization of allenoates with iodoalkynes for the synthesis of β-alkynyl-γbutenolides. Organic Chemistry Frontiers, 2024, 11, pp.5695. ⟨10.1039/D4QO01153H⟩. ⟨hal-04797045⟩
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