Revealing the electrophilicity of N-Ac indoles with FeCl3: a mechanistic study

Revealing the electrophilicity of N-Ac indoles with FeCl3: a mechanistic study

Herein, we report a mechanistic exploration of the unusual FeCl3-mediated hydroarylation of N-Ac indoles. Electron density topology analysis of a crystal, in situ IR monitoring, Hammett and Taft studies as well as DFT computations allowed us to determine that activation of acetyl with FeCl3 and of t...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2017-05, Vol.53 (43), p.5834-5837
Hauptverfasser: Beaud, Rodolphe, Nandi, Raj Kumar, Perez-Luna, Alejandro, Guillot, Régis, Gori, Didier, Kouklovsky, Cyrille, Ghermani, Nour-Eddine, Gandon, Vincent, Vincent, Guillaume
Format: Artikel
Sprache:eng
Schlagworte:
Activation analysis
Bonding
Crystals
Electron density
Exploration
Indoles
Infrared radiation
Monitoring
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Beschreibung
Zusammenfassung:Herein, we report a mechanistic exploration of the unusual FeCl3-mediated hydroarylation of N-Ac indoles. Electron density topology analysis of a crystal, in situ IR monitoring, Hammett and Taft studies as well as DFT computations allowed us to determine that activation of acetyl with FeCl3 and of the C2[double bond, length as m-dash]C3 bond with a proton is involved.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc02756g