Revealing the electrophilicity of N-Ac indoles with FeCl3: a mechanistic study. Issue 43 (12th May 2017)

• Record Type: Journal Article
• Authors: Beaud, Rodolphe; Nandi, Raj Kumar; Perez-Luna, Alejandro; Guillot, Régis; Gori, Didier; Kouklovsky, Cyrille; Ghermani, Nour-Eddine; Gandon, Vincent; Vincent, Guillaume
• Is Part Of: Chemical communications. Volume 53:Issue 43(2017)
• Page Start: 5834
• Page End: 5837
• Publication Date: 2017-05-12
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c7cc02756g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The puzzling hydroarylation of N -Ac indoles promoted by iron trichloride involves a doubly activated intermediate: as supported by the electron density topology of a crystal, IR monitoring, and DFT calculations. Abstract : 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C3 bond with a proton is involved.