Direct condensation of sulfonamide and formamide: NaI-catalyzed synthesis of N-sulfonyl formamidine using TBHP as oxidant

Org Lett. 2011 Dec 2;13(23):6152-5. doi: 10.1021/ol2024604. Epub 2011 Oct 31.

Abstract

A new N-sulfonyl formamidine synthesis was developed via NaI-catalyzed direct condensation of sulfonamide and formamide. The green methodology is featured by high atom economy, easily available starting materials, the lack of need for a transition-metal catalyst, no requirement of hazardous reagent, operational simplicity, and good tolerance with diverse functional groups. Mechanistic studies suggest that the protocol proceeds based upon in situ generated TsN·NaI.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidines / chemical synthesis*
  • Amidines / chemistry
  • Catalysis
  • Formamides / chemistry*
  • Molecular Structure
  • Oxidants / chemistry*
  • Sulfonamides / chemistry*

Substances

  • Amidines
  • Formamides
  • Oxidants
  • Sulfonamides
  • formamidine
  • formamide