Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles

Abstract

Sourcing nitrogen from nitromethane Nitromethane is produced in bulk quantities for use as a solvent. Its applications as a reagent have focused mainly on the acidity of the methyl protons en route to modifying the carbon center. Liu et al. now report an alternative protocol that activates the nitrogen center to produce an aminating agent. An in situ reductive reaction with triflic anhydride, formic acid, and acetic acid yields an acetylated hydroxylamine, characterized by mass spectrometry. This nitrogen donor conveniently transforms a variety of ketones and aldehydes into amides. Science , this issue p. 281