Accessing pyrrolo[1,2-<i>a</i>]indole derivatives <i>via</i> visible-light-induced dearomatizative cyclization of indoles

Liu, Zhaosheng; Ji, Xiaochen; Duan, Lilan; Deng, Guo-Jun; Huang, Huawen

doi:10.1039/d4cc01215a

Chem. Commun.

2024

DOI: 10.1039/d4cc01215a

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Accessing pyrrolo[1,2-a]indole derivatives via visible-light-induced dearomatizative cyclization of indoles

Zhaosheng Liu,

Xiaochen Ji,

Lilan Duan

et al.

Abstract: Pyrrolo[1,2-a]indoles are structurally important scaffolds in many natural products and bioactive compounds. Herein, we report a novel synthetic method for pyrrolo[1,2-a]indole derivatives through visible-light-induced cascade dearomatizative cyclization of indoles with...

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Cited by 3 publications

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Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles

Machín Rivera,

Ferrin,

Lindsay

2024

Org. Lett.

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A concise synthetic approach to medicinally relevant pyrroloindolones and related fused heterocycles is reported via the diastereoselective N-addition of unprotected indoles to readily accessible cyclopropanone equivalents. The resulting stable hemiaminals are shown to smoothly rearrange to pyrroloindolones in mild conditions using Fe(III) catalysis in the presence of inexpensive ammonium persulfate as a stoichiometric oxidant. Experimental evidence points toward the formation of a β-carboxylic radical intermediate prone to cyclization and oxidative rearomatization as the operative mechanistic pathway.

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Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles

Machín Rivera,

Ferrin,

Lindsay

2024

Org. Lett.

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Photoredox-Catalyzed Markovnikov Hydroamination of Alkenes with Azoles

Nie,

Shi,

Gan

et al. 2024

Org. Lett.

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Access to tetrahydrocarbazoles via a photocatalyzed cascade decarboxylation/addition/cyclization reaction

Han,

Chen,

Guo

et al. 2024

Org. Chem. Front.

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Accessing pyrrolo[1,2-a]indole derivatives via visible-light-induced dearomatizative cyclization of indoles

Abstract: Pyrrolo[1,2-a]indoles are structurally important scaffolds in many natural products and bioactive compounds. Herein, we report a novel synthetic method for pyrrolo[1,2-a]indole derivatives through visible-light-induced cascade dearomatizative cyclization of indoles with...

Cited by 3 publications

References 28 publications

Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles

Iron-Catalyzed Oxidative Rearrangement of Cyclopropanone Hemiaminals: General Access to Pyrroloindolones from Indoles

Photoredox-Catalyzed Markovnikov Hydroamination of Alkenes with Azoles

Access to tetrahydrocarbazoles via a photocatalyzed cascade decarboxylation/addition/cyclization reaction

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