Sulfonamides, sulfamides, and sulfamates are critically important compounds with therapeutic applications against cancer, HIV, and microbial infections. Current strategies toward these nitrogen-based sulfur(VI) compounds are limited by the commercial availability or stability of starting materials, and harsh reactions preventing late-stage functionalization. Sulfur-fluoride exchange (SuFEx) chemistry is a promising new pathway to synthesize sulfonylated products from sulfur(VI) fluorides and nucleophiles. Although, the stability of sulfur(VI) fluorides compared to other halogen analogues present challenges for synthetic applications. A new SuFEx reaction to synthesize nitrogen-based sulfonylated compounds from a variety of S(VI) fluorides mediated via a Lewis acidic calcium salt will be described. Under a unified set of reaction conditions, sulfonyl fluorides, fluorosulfates, and sulfamoyl fluorides can be coupled with a variety of amines to synthesis a diverse array of aryl and alkyl sulfonamides, sulfamides, and sulfamates in good to excellent yield. Notably alkyl sulfamoyl fluorides –the most stable S(VI) fluorides – can undergo SuFEx chemistry at room temperature in good yield. Applications toward parallel synthesis to access structurally diverse S(VI) compounds will also be discussed.

Ca-mediated SuFEx reaction toward the synthesis of sulfamides, sulfamates, and sulfonamides from S(VI) fluorides

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.