Preparation of sulfonamides from N-silylamines

Rajasekhar Reddy Naredla, Douglas A. Klumpp

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Sulfonamides have been prepared in high yields by the reactions of N-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.

Original languageEnglish (US)
Pages (from-to)5945-5947
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number45
DOIs
StatePublished - Nov 6 2013

Keywords

  • N-Silylamine
  • Substitution
  • Sulfonamides
  • Sulfonyl transfer

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