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Issue 55, 2018
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The triple role of rongalite in aminosulfonylation of aryldiazonium tetrafluoroborates: synthesis of N-aminosulfonamides via a radical coupling reaction

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Abstract

A simple and convenient method for N-aminosulfonamide synthesis from the cross-coupling of aryldiazonium tetrafluoroborates and rongalite under metal-free, oxidant-free, and room-temperature conditions is reported. This method does not require an external amine source, with the aryldiazonium tetrafluoroborates participating as both an aryl radical and a potential amine source in the transformation. Mechanistic studies revealed that rongalite could act as a radical initiator, a sulfur dioxide surrogate and a reducing reagent simultaneously in this reaction.

Graphical abstract: The triple role of rongalite in aminosulfonylation of aryldiazonium tetrafluoroborates: synthesis of N-aminosulfonamides via a radical coupling reaction

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Publication details

The article was received on 10 May 2018, accepted on 14 Jun 2018 and first published on 14 Jun 2018


Article type: Communication
DOI: 10.1039/C8CC03778G
Citation: Chem. Commun., 2018,54, 7641-7644
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    The triple role of rongalite in aminosulfonylation of aryldiazonium tetrafluoroborates: synthesis of N-aminosulfonamides via a radical coupling reaction

    M. Wang, B. Tang, J. Wang, J. Xiang, A. Guan, P. Huang, W. Guo, Y. Wu and A. Wu, Chem. Commun., 2018, 54, 7641
    DOI: 10.1039/C8CC03778G

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