Light‐Promoted Germylation of Aryl Propiolamides/Alkynoates: Synthesis of Ge‐Containing Spiro[4.5]trienones and Vinylgermanes

Luo, Yani; Lv, Leiyang; Li, Zhiping

doi:10.1002/cctc.202300467

ChemCatChem

2023

DOI: 10.1002/cctc.202300467

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Light‐Promoted Germylation of Aryl Propiolamides/Alkynoates: Synthesis of Ge‐Containing Spiro[4.5]trienones and Vinylgermanes

Yani Luo

Leiyang Lv

Zhiping Li

Abstract: The light-promoted regioselective germylation of aryl propiolamides/alkynoates with germanium hydrides is reported. The germyl-containing spiro[4.5]trienones were obtained when N-arylpropiolamides were used via sequential CÀ Ge and CÀ C bond formation, while aryl alkynoates delivered the vinylgermanes with radical Smiles rearrangement and CO 2 release.

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2024

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Cited by 3 publications

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Visible‐Light‐Driven Germyl Radical Generation via EDA‐Catalyzed ET–HAT Process

Yoshizawa,

Li,

Matsuyama

et al. 2024

Chemistry A European J

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We have established a facile and efficient protocol for the generation of germyl radicals by employing photo‐excited electron transfer (ET) in an electron donor‐acceptor (EDA) complex to drive hydrogen‐atom transfer (HAT) from germyl hydride (R3GeH). Using a catalytic amount of EDA complex of commercially available thiol and benzophenone derivatives, the ET‐HAT cycle smoothly proceeds simply upon blue‐light irradiation without any transition metal or photocatalyst. This protocol also affords silyl radical from silyl hydride.

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Visible‐Light‐Driven Germyl Radical Generation via EDA‐Catalyzed ET–HAT Process

Yoshizawa,

Li,

Matsuyama

et al. 2024

Chemistry A European J

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Photoinduced Palladium-Catalyzed Radical Germylative Arylation of Alkenes with Chlorogermanes

Wang,

Zhang,

Cao

et al. 2024

J. Org. Chem.

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We describe a visible light-induced palladium-catalyzed radical germylative arylation of alkenes with easily accessible chlorogermanes. This protocol provides expedient access to germanium-substituted indolin-2-ones in good to excellent yields under mild reaction conditions. The key step for this strategy lies in the reductive activation of germanium–chloride bonds with an excited palladium complex under visible light irradiation. The involvement of germanium radicals was evidenced by electron paramagnetic resonance spectroscopy experiments.

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Photoinduced decarboxylative germylation of α-fluoroacrylic acids: access to germylated monofluoroalkenes

Lu,

Qian,

Sun

et al. 2024

Chem. Commun.

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Light‐Promoted Germylation of Aryl Propiolamides/Alkynoates: Synthesis of Ge‐Containing Spiro[4.5]trienones and Vinylgermanes

Cited by 3 publications

References 82 publications

Visible‐Light‐Driven Germyl Radical Generation via EDA‐Catalyzed ET–HAT Process

Visible‐Light‐Driven Germyl Radical Generation via EDA‐Catalyzed ET–HAT Process

Photoinduced Palladium-Catalyzed Radical Germylative Arylation of Alkenes with Chlorogermanes

Photoinduced decarboxylative germylation of α-fluoroacrylic acids: access to germylated monofluoroalkenes

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