Sulfonyl fluorides are an emerging class of compounds that have applications from chemical biology to medicinal chemistry. The thermal and hydrolytic stability of S(VI)–F bonds make sulfonyl fluorides an attractive alternative to sulfides or sulfonyl chlorides as starting materials towards sulfonamides. A challenge with using sulfonyl fluorides as precursors to sulfonamides is that small permutations in the structure of sulfonyl fluoride or amine require markedly different reaction conditions for the conversion to occur. To address this challenge, we have developed a Lewis acid meditated method that can convert a diverse array of aryl and alkyl sulfonyl fluorides to sulfonamides in good to excellent yields. Group 2 Lewis acids have been demonstrated to be the most effective in this method. Application of this method towards heterocyclic sulfonamides and complex sulfonamides will also be discussed. Efforts leading to the development of a collaborative industrial/undergraduate research program will also be highlighted.

Lewis acid mediated activation of aryl and alkyl sulfonyl fluorides towards sulfonamides

255th National Meeting (2018)

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