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Issue 23, 2016
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Electrochemically initiated formation of sulfonyl radicals: synthesis of oxindoles via difunctionalization of acrylamides mediated by bromide ion

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Abstract

An efficient electrochemical approach for the synthesis of oxindoles has been developed from electrolysis of a mixture of sodium sulfinate and acrylamide. The chemistry avoids the utilization of additional conducting salt and proceeds in a simple undivided cell employing a catalytic amount of NH4Br (10 mmol%) as a redox catalyst. The protocol is practical, as proved by the one-pot, two-step procedure and scaled-up experiments. Mechanistic studies reveal that the electrochemical approach involves the formation of sulfonyl radicals via homolytic cleavage of in situ generated sulfonyl bromide.

Graphical abstract: Electrochemically initiated formation of sulfonyl radicals: synthesis of oxindoles via difunctionalization of acrylamides mediated by bromide ion

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Publication details

The article was received on 20 Jul 2016, accepted on 09 Sep 2016 and first published on 09 Sep 2016


Article type: Paper
DOI: 10.1039/C6GC01970F
Citation: Green Chem., 2016,18, 6311-6319
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    Electrochemically initiated formation of sulfonyl radicals: synthesis of oxindoles via difunctionalization of acrylamides mediated by bromide ion

    Y. Jiang, S. Liang, C. Zeng, L. Hu and B. Sun, Green Chem., 2016, 18, 6311
    DOI: 10.1039/C6GC01970F

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