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

Abstract

Aliphatic and aromatic amines undergo smooth nucleophilic addition to a,b-unsaturated compounds in the presence of a catalytic amount of silicasupported aluminum chloride at 60 C and under solvent-free conditions to produce the corresponding b-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.

Synthesis and characterization of bile acid‐based poly β amino esters for paclitaxel delivery

“…19–21 Lewis acids (e.g., AlCl 3 ) are known to accelerate electrophilic reactions in organic chemistry. 22–24 In the present case, AlCl 3 on addition to diacrylate solution formed coordinate complex with carbonyl oxygen of acrylate esters. Once this complex was formed the electronic resonance across ester bond resulted in the generation of stable electrophilic center at olefinic methylene which favored nucleophilic addition of amines.…”

Hydrotreating of Light Cycle Oil over Supported on Porous Aromatic Framework Catalysts

“…Recently, we described the synthesis of a PAF-AlCl 3 catalyst and its use in the hydrogenation-hydrocracking of naphthalene [19]. It is well known that Lewis acids, particularly aluminum chloride, react with aromatic substances and form complexes of the type PhH σ+ -(AlCl 3 ) σ− through charge-transfer mechanisms [25][26][27]. We showed that this mechanism was realized also in the case of the interaction between AlCl 3 and PAF.…”

Supported TBD-Assisted Solution Phase Diversification of Formyl-Aza-Heterocycles Through Alkylation-Knoevenagel One Pot Sequences

“…As an alternative to these reagents and considering its reported application in Aza-Michael [23] and Knoevenagel reactions [15] of its supported version, the silica-aluminium chloride (6) was also tested as versatile and effective catalyst for the Aza-Michael-Knoevenagel sequences.…”