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Issue 14, 2019
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Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles

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Abstract

Environmentally benign electrochemically enabled chemoselective sulfonylation and hydrazination of C2,C3-unsubstituted indoles with arylsulfonyl hydrazide in the presence of ammonium bromide as a redox catalyst and electrolyte have been demonstrated in this work. Under mild electro-oxidation conditions, a series of indole hydrazination products with pharmacological activity were obtained. In vitro, the hydrazination products exhibited a better anti-cancer activity compared with the diazotization products. Further mechanistic studies showed that compound 3ae inhibits cell migration and tubulin aggregation in T-24 cells, thereby leading to cell apoptosis.

Graphical abstract: Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles

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Publication details

The article was received on 12 Apr 2019, accepted on 25 Jun 2019 and first published on 26 Jun 2019


Article type: Communication
DOI: 10.1039/C9GC01201J
Green Chem., 2019,21, 3807-3811

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    Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles

    Y. Zhang, Z. Mo, H. Wang, X. Wen, H. Tang and Y. Pan, Green Chem., 2019, 21, 3807
    DOI: 10.1039/C9GC01201J

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