Sustainable and versatile Aza-Michael additions promoted by acidic ionic liquids

Abstract

Acidic ionic liquids are a subset of ionic liquids where the cation or anion possess acidic properties with huge applications in various fields. Here we describe environmentally safe and highly efficient conjugate addition of aromatic and aliphatic amines to α, β-unsaturated compounds in the presence of novel acidic ionic liquids. The acidic ionic liquid catalyst was prepared by combining benzyl chloride with 2-(dimethylamino) ethanol and SnCl2 in a simpler manner. The resulting acidic ionic liquid was characterized using SEM, EDS and FTIR spectroscopy. In the presence of ionic liquids, a wide variety of amines undergo facile conjugate addition to α, β-unsaturated compounds affording the corresponding β-amino compounds in good to excellent yields (72–97 %), shorter reaction times (1–4 h) and mild reaction conditions (60 °C). Furthermore, the study demonstrated the sustainability of the process by showcasing that the acidic ionic liquids could be reclaimed and reused for up to five cycles without compromising their catalytic effectiveness.

Keywords

• Acidic ionic liquids
• Aza-Michael addition
• Green chemistry
• Amine adduct