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2016-01-28

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Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/127808

Pd-Catalyzed α-Arylation of Sulfones in a Three-Component Synthesis of 3-[2-(Phenyl/methylsulfonyl)ethyl]indoles

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Recurs relacionat

https://doi.org/10.1021/acscatal.6b00027

Resum

A novel four-step domino process for the synthesis of 3-[2-(aryl/alkylsulfonyl)ethyl]indoles starting from readily available 2-iodoanilines is reported. The domino reaction is based on the intramolecular palladium-catalyzed α-arylation of sulfones, which was combined with both intermolecular aza-Michael and Michael addition reactions using vinyl sulfones as the electrophile. The domino process produced good yields and tolerated the presence of substituents with different electronic properties on the aniline ring. In addition, density functional theory (DFT) calculations were carried out to gain more insight into the formation of the observed indole derivatives. Keywords: arylation; density functional calculations; domino reactions; indoles; palladium-catalyzed

Matèries

Pal·ladi (Element químic), Catàlisi, Teoria del funcional de densitat, Compostos heterocíclics, Síntesi orgànica

Matèries (anglès)

Palladium, Catalysis, Density functionals, Heterocyclic compounds, Organic synthesis

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

Citació

SOLÉ ARJÓ, Daniel, et al. Pd-Catalyzed α-Arylation of Sulfones in a Three-Component Synthesis of 3-[2-(Phenyl/methylsulfonyl)ethyl]indoles. ACS Catalysis. 2016. Vol. 6, num. 3, pags. 1691-1700. ISSN 2155-5435. [consulted: 24 of May of 2026]. Available at: https://hdl.handle.net/2445/127808

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