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

Rodolphe Beaud; Raj Kumar Nandi; Alejandro Perez-Luna; Régis Guillot; Didier Gori; Cyrille Kouklovsky; Nour-Eddine Ghermani; Vincent Gandon; Guillaume Vincent

doi:10.1039/C7CC02756G

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

Rodolphe Beaud,‡^a Raj Kumar Nandi,‡^a Alejandro Perez-Luna,

^b Régis Guillot,

^a Didier Gori,^a Cyrille Kouklovsky,^a Nour-Eddine Ghermani,*^cd Vincent Gandon

*^ae and Guillaume Vincent

*^a

Author affiliations

* Corresponding authors

^a Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Univ. Paris-Sud, Université Paris-Saclay, CNRS UMR 8182, 91405 Orsay cedex, France
E-mail: guillaume.vincent@u-psud.fr

^b Sorbonne Universités, UPMC Univ Paris 06, CNRS UMR 8232, Institut Parisien de Chimie Moléculaire (IPCM), FR 2769, Case 229, 4 place Jussieu, 75005 Paris, France

^c Laboratoire Structures, Propriétés et Modélisation des Solides, Université Paris Saclay, Centrale Supélec, CNRS, UMR 8580, Grande voie des vignes, 92295 Châtenay-Malabry, France

^d Laboratoire de Physique Pharmaceutique, Institut Galien Paris Sud, UMR CNRS 8612, Univ. Paris Sud, Faculté de Pharmacie, Université Paris-Saclay, 5 rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France
E-mail: noureddine.ghermani@u-psud.fr

^e Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France
E-mail: vincent.gandon@u-psud.fr

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 [double bond, length as m-dash] C3 bond with a proton is involved.

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Article information

DOI: https://doi.org/10.1039/C7CC02756G
Article type: Communication
Submitted: 10 Apr 2017
Accepted: 01 May 2017
First published: 03 May 2017

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Chem. Commun., 2017,53, 5834-5837

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

R. Beaud, R. K. Nandi, A. Perez-Luna, R. Guillot, D. Gori, C. Kouklovsky, N. Ghermani, V. Gandon and G. Vincent, Chem. Commun., 2017, 53, 5834 DOI: 10.1039/C7CC02756G

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