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Metal-Free Construction of Primary Sulfonamide through Three Diverse Salts

Abstract

In this report, the first metal-free construction of primary sulfonamide through a direct three-component reaction of sodium metabisulfite, sodium azide and aryldiazonium was established. The readily available inorganic Na2S2O5 and NaN3 were applied for 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 installed with –SO2NH2 group efficiently at late stage. Control experiments and kinetic studies demonstrated that aryl radical, sulfonyl radical and conjugated phosphine imine radical involved in this transformation.

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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, Accepted Manuscript
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    Metal-Free Construction of Primary Sulfonamide through Three Diverse Salts

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

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