The most common method for the synthesis of sulfonamides remains unchanged from that used for the preparation of the first “sulfa drug”, Prontosil, in the 1930’s. The key reaction combines an amine with a sulfonyl chloride, and although this is robust methodology, it is limited by the stability and availability of specific sulfonyl chlorides. We have been interested in alternative approaches to sulfonamides, and in particular, in routes that avoid the need to employ substrates with pre-installed sulfur functionality. We have focused on syntheses that involve the insertion of a molecule of sulfur dioxide between appropriate carbon and nitrogen fragments, and have developed a series of transformations that exploit the sulfur dioxide surrogate reagent DABSO. This includes a sulfonamide synthesis based on the direct union of aryl boronic acids, DABSO, and amines, using a Cu(II) catalyst. The development of these reactions, as well as recent advances, will be discussed.

Sulfonamide syntheses exploiting sulfur dioxide insertion

ACS Fall 2020 Virtual Meeting

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