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

He, Yuanhao; Zhong, Yu; Marion, Maria Ballarin; Luna, Jorge C. Herrera; Ma, Wanping; Hu, Yanfei; Ollivier, Cyril; Mouriès-Mansuy, Virginie; Fensterbank, Louis; Zhao, Fen; Xia, Zhonghua; Fan, Baomin

doi:10.1039/d4qo01153h

Org. Chem. Front.

2024

DOI: 10.1039/d4qo01153h

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

Yuanhao He,

Yu Zhong,

Maria Ballarin Marion

et al.

Abstract: A method for the tandem cyclization/alkynylation of allenoates with iodoalkynes via gold catalysis under light irradiation is described. Mechanistic studies support that an energy-transfer event takes place, rather than a redox pathway.

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Cited by 3 publications

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Formation of 3-Alkynylidenephthalides by Gold(I)-Catalyzed Alkynylative Cyclization of o-Alkynylbenzoic Acids under Visible Light Irradiation

Ballarín-Marión,

Herrera-Luna,

Corcé

et al. 2024

J. Org. Chem.

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Herein, we report a Csp 2 −Csp cross-coupling process involving the merger of gold catalysis and visible light photocatalysis leading to the alkynylative cyclization of o-alkynyl benzoic acids. The corresponding and previously undescribed alkynylidenephthalide products were obtained as mixtures of E:Z isomers. The key C−C bond formation is based on the photoactivation of the oxidative addition of an alkynyliodide to a vinylgold(I) intermediate resulting from an initial 5-exo-dig cyclization pathway, as supported by mechanistic studies including DFT calculations.

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Formation of 3-Alkynylidenephthalides by Gold(I)-Catalyzed Alkynylative Cyclization of o-Alkynylbenzoic Acids under Visible Light Irradiation

Ballarín-Marión,

Herrera-Luna,

Corcé

et al. 2024

J. Org. Chem.

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Synthesis of tetrasubstituted furans through a Cu/base-mediated cascade reaction from terminal alkynes and 1,2-diketones

Fan,

Liang,

Yao

et al. 2025

Org. Biomol. Chem.

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Hemilabile P,N-ligand-assisted gold catalyzed Hiyama allylation to access allylarenes and 1,4-diene derivatives

He,

Ma,

Zhong

et al. 2025

Org. Chem. Front.

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

Abstract: A method for the tandem cyclization/alkynylation of allenoates with iodoalkynes via gold catalysis under light irradiation is described. Mechanistic studies support that an energy-transfer event takes place, rather than a redox pathway.

Cited by 3 publications

References 60 publications

Formation of 3-Alkynylidenephthalides by Gold(I)-Catalyzed Alkynylative Cyclization of o-Alkynylbenzoic Acids under Visible Light Irradiation

Formation of 3-Alkynylidenephthalides by Gold(I)-Catalyzed Alkynylative Cyclization of o-Alkynylbenzoic Acids under Visible Light Irradiation

Synthesis of tetrasubstituted furans through a Cu/base-mediated cascade reaction from terminal alkynes and 1,2-diketones

Hemilabile P,N-ligand-assisted gold catalyzed Hiyama allylation to access allylarenes and 1,4-diene derivatives

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