title: Preparation of sulfonamides fromN-silylamines.
abstract: Sulfonamides have been prepared in high yields by the reactions ofN-silylamines with sulfonyl chlorides and fluorides. In a competition experiment, the sulfonyl chlorides were found to be far more reactive than sulfonyl fluorides. The chemistry may be used to prepare aliphatic, aromatic, tertiary, secondary, and primary sulfonamides. It may also be done in the absence of solvent and the byproduct trimethylsilyl chloride recovered in good yield. Primary sulfonamides were synthesized from the sulfonyl chloride with aminotriphenyl silane (Ph3SiNH2), a conversion demonstrated with the synthesis of the carbonic anhydrase inhibitor, acetazolamide.
authors.affiliation: Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115.
authors.forename: Rajasekhar Reddy
authors.initials: RR
authors.lastname: Naredla
authors.affiliation: Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60115.
authors.forename: Douglas A
authors.initials: DA
authors.lastname: Klumpp
keywords: N-silylamine; Sulfonamides; substitution; sulfonyl transfer