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A general electrochemical strategy for the Sandmeyer reaction

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Abstract

Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl3, CH2I2, CCl4, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and in situ electron paramagnetic resonance (EPR) analysis.

Graphical abstract: A general electrochemical strategy for the Sandmeyer reaction

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Publication details

The article was received on 27 Jul 2018, accepted on 17 Sep 2018 and first published on 17 Sep 2018


Article type: Edge Article
DOI: 10.1039/C8SC03346C
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    A general electrochemical strategy for the Sandmeyer reaction

    Q. Liu, B. Sun, Z. Liu, Y. Kao, B. Dong, S. Jiang, F. Li, G. Liu, Y. Yang and F. Mo, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C8SC03346C

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