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Issue 43, 2017
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Revealing the electrophilicity of N-Ac indoles with FeCl3: a mechanistic study

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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.

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

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Publication details

The article was received on 10 Apr 2017, accepted on 01 May 2017 and first published on 03 May 2017


Article type: Communication
DOI: 10.1039/C7CC02756G
Citation: 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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