Solvent effects in the aza-Michael addition of anilines

Abstract

The aza-Michael addition of functionally substituted anilines to enoates is significantly affected by the hydrogen bond donor ability of the solvent. Very polar protic fluorinated alcohols (hexafluoroisopropanol and trifluoroethanol) favor the addition of weak nucleophiles, whereas these solvents are no longer required for anilines bearing additional OH or NH 2 group.