Highly Efficient Michael Addition Reaction of Amines Catalyzed by Silica-Supported Aluminum Chloride

Abstract

Aliphatic and aromatic amines undergo smooth nucleophilic addition to α,β-unsaturated compounds in the presence of a catalytic amount of silica-supported aluminum chloride at 60 °C and under solvent-free conditions to produce the corresponding β-amino compounds in excellent yields. This method is simple and convenient and works efficiently under mild conditions. This catalyst can used again without losing its activity three times.

Keywords:

• Amines
• Michael addition
• silica-supported aluminum chloride
• α,β-unsaturated olefins

Notes

^a 96% mono-substitution and 4% bis-substitution products.

^b 100% bis-substitution.

^c Three equivalents of Michael acceptor were used.

^a 1 mmol aniline, 1.5 mmol methy1 acrylate, and 0.2 g silica-supported aluminum chloride were used each time.