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Issue 24, 2018
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Metal-free construction of primary sulfonamides through three diverse salts

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Abstract

In this report, the first metal-free construction of primary sulfonamides through a direct three-component reaction of sodium metabisulfite, sodium azide and aryldiazonium has been established. Readily available inorganic Na2S2O5 and NaN3 were applied as the sulfur dioxide surrogate and nitrogen source respectively. The widely used sulfonamide drugs Celecoxib and Sulpiride, which possess multiple heteroatoms and active hydrogen containing functional groups, are efficiently installed with –SO2NH2 groups at a late stage. Control experiments and kinetic studies demonstrated that aryl radicals, sulfonyl radicals and conjugated phosphine imine radicals are involved in this transformation.

Graphical abstract: Metal-free construction of primary sulfonamides through three diverse salts

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Publication details

The article was received on 25 Sep 2018, accepted on 07 Nov 2018 and first published on 07 Nov 2018


Article type: Communication
DOI: 10.1039/C8GC03014F
Citation: Green Chem., 2018,20, 5469-5473
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    Metal-free construction of primary sulfonamides through three diverse salts

    M. Wang, Q. Fan and X. Jiang, Green Chem., 2018, 20, 5469
    DOI: 10.1039/C8GC03014F

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