A general, mild, convenient and environmentally benign method was developed for the synthesis of various N-aryl and N-alkyl sulfonamides in water. Trichloroisocyanuric acid (TCCA) was used for the oxidative chlorination of disulfides and thiols to produce the corresponding sulfonyl chloride, which reacted in situ with different amines in the absence of organic bases, to furnish sulfonamides in good to excellent yields. The isolation of the products involves simple experimental conditions and a product isolation procedure (only filtration) in the absence of organic solvents, which makes this protocol potentially useful in the development of a green strategy for the synthesis of sulfonamides.
The method employs trichloroisocyanuric acid for the oxidative chlorination of disulfide (I) to produce the corresponding sulfonyl chloride in the first step.
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