N-(tert-butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide: a convenient sulfamoylation reagent for alcohols

Org Lett. 2012 May 18;14(10):2626-9. doi: 10.1021/ol3009683. Epub 2012 May 9.

Abstract

A convenient and efficient procedure is described for the sulfamoylation of alcohols using N-(tert-butoxycarbonyl)-N-[(triethylenediammonium)sulfonyl]azanide (1). The ambient temperature stable reagent 1 reacts with phenols as well as primary and secondary alcohols to give high to modest yields. The relative reaction rate of substrates was determined (primary > phenol > secondary ≫ tertiary). The reagent's utility as a selective sulfamoylation reagent with polyols is also demonstrated.

MeSH terms

  • Alcohols / chemistry*
  • Amines
  • Indicators and Reagents
  • Molecular Structure
  • Phenols
  • Sulfones / chemistry*

Substances

  • Alcohols
  • Amines
  • Indicators and Reagents
  • N-(tert-butoxycarbonyl)-N-((triethylenediammonium)sulfonyl)azanide
  • Phenols
  • Sulfones