Revealing the electrophilicity of N-Ac indoles with FeCl _\textrm3 : a mechanistic study

Rodolphe Beaud (1) , Raj Kumar Nandi (1) , Alejandro Perez-Luna (2) , Régis Guillot (1) , Didier Gori (1) , Cyrille Kouklovsky (1) , Nour-Eddine Ghermani (3, 4) , Vincent Gandon (5, 1) , Guillaume Vincent (1)

1 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay
2 ROCS - Réactivité organométallique et catalyse pour la synthèse
3 SPMS - Laboratoire Structures, Propriétés et Modélisation des solides
4 IGPS - Institut Galien Paris-Sud
5 ICSN - Institut de Chimie des Substances Naturelles

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 C2C3 bond with a proton is involved.

Domaines: Chimie

Rodolphe Beaud, Raj Kumar Nandi, Alejandro Perez-Luna, Régis Guillot, Didier Gori, et al.. Revealing the electrophilicity of N-Ac indoles with FeCl _\textrm3 : a mechanistic study. Chemical Communications, 2017, 53 (43), pp.5834--5837. ⟨10.1039/C7CC02756G⟩. ⟨hal-01712357⟩