Literature DB >> 28497835

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

Rodolphe Beaud1, Raj Kumar Nandi, Alejandro Perez-Luna, Régis Guillot, Didier Gori, Cyrille Kouklovsky, Nour-Eddine Ghermani, Vincent Gandon, Guillaume Vincent.   

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.

Entities:  

Year:  2017        PMID: 28497835     DOI: 10.1039/c7cc02756g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  1 in total

1.  Unbiased C3-Electrophilic Indoles: Triflic Acid Mediated C3-Regioselective Hydroarylation of N-H Indoles.

Authors:  Nazarii Sabat; Weiping Zhou; Vincent Gandon; Xavier Guinchard; Guillaume Vincent
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-02       Impact factor: 16.823

  1 in total

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