Synthesis of Thienyl Polycyclic Fused Indoles Based on the Indium Catalyzed Prins/Friedel‐Crafts Tandem Reaction

Zhi-jian, Huang; Zhao, Min; Xu, Lingfeng; Wang, Lijia

doi:10.1002/ajoc.202300147

Cited by 3 publications

(1 citation statement)

References 27 publications

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“…Furthermore, the biological activity of thienyl polycyclic fused indole frameworks and the utility of this reaction technique in organic synthesis are now being studied by Wang's group. [13]…”

Section: Annulationmentioning

confidence: 99%

Indium Triflate's Transformative Role in Modern Organic Synthesis: A Five‐Year Survey of Functionalization, Cyclization, and Multicomponent Reactions

Jamshaid

2024

ChemistrySelect

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Indium triflate (In(OTf)3) has proven to be a powerful and sustainable catalyst in the synthesis of modern organic compounds, enabling a variety of transformations such as functionalization, cyclization, and multicomponent reactions. To provide insight into the most recent methods and applications, this study attempts to provide a comprehensive and up‐to‐date summary of these advances in the application of indium triflate as a catalyst in organic synthesis, focusing on the last five years of literature. The application of indium triflate as opposed to alternative indium(III) catalysts in organic transformations will be the main emphasis of this review, which will cover recent developments through research articles and reviews published between 2019 and 2023. This minireview will make a significant contribution to the existing literature by consolidating recent advancements in the use of indium triflate in modern organic synthesis.

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Section: Annulationmentioning

confidence: 99%

Indium Triflate's Transformative Role in Modern Organic Synthesis: A Five‐Year Survey of Functionalization, Cyclization, and Multicomponent Reactions

Jamshaid

2024

ChemistrySelect

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Chemodivergent Reactions of Aromatic Ring-Annulated Hexahydrocyclopentafurans with Various Aldehydes

Kindala,

Yano,

Takatori

et al. 2024

Org. Lett.

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furan fused to electron-rich aromatic rings reacts with various aromatic aldehydes in different modes to build diverse frameworks. The reaction of a dimethoxybenzene-fused cyclopentafuran generated diquinanes fused with a hydrofuran ring, indenopyrans, or diarylindanes depending upon the type of aromatic aldehydes, whereas an indole-annulated cyclopentafuran generated another type of diquinane fused with hydrofuran ring or benzylidenecyclopentafuran. The chemodivergence is due to the different properties between indole-and dimethoxybenzene-fused hydrocyclopentafurans. Namely, Lewis acid-promoted furan-ring opening of the substrates resulted in the formation of an electrophilic or a nucleophilic intermediate, respectively. Additionally, the observed chemodivergence can be attributed to the distinctive electronic properties of three classified aromatic aldehydes. Of particular interest is that 2,4-dimethoxybenzaldehyde reacted with the dimethoxybenzene-fused cyclopentafuran at the benzene ring, whereas it reacted with the indole-fused cyclopentafuran at the formyl group.

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Advances in the Study of the Prins Reaction and the Prins Cyclization Reaction

丹

2024

JOCR

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Synthesis of Thienyl Polycyclic Fused Indoles Based on the Indium Catalyzed Prins/Friedel‐Crafts Tandem Reaction

Cited by 3 publications

References 27 publications

Indium Triflate's Transformative Role in Modern Organic Synthesis: A Five‐Year Survey of Functionalization, Cyclization, and Multicomponent Reactions

Indium Triflate's Transformative Role in Modern Organic Synthesis: A Five‐Year Survey of Functionalization, Cyclization, and Multicomponent Reactions

Chemodivergent Reactions of Aromatic Ring-Annulated Hexahydrocyclopentafurans with Various Aldehydes

Advances in the Study of the Prins Reaction and the Prins Cyclization Reaction

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