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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 6
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Original Articles

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

, &
Pages 1109-1119 | Received 02 Jul 2008, Published online: 25 Feb 2009
 

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.

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.

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