Metal-organic framework MIL-53(Al): synthesis, catalytic performance for the Friedel-Crafts acylation, and reaction mechanism  

作　　者：Junlei Yan Sai Jiang Shengfu Ji Da Shi Hefei Cheng 

机构地区：[1]State Key Laboratory of Chemical Resource Engineering [2]Beijing University of Chemical Technology

出　　处：《Science China Chemistry》2015年第10期1544-1552,共9页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(21136001,21173018)

摘　　要：Metal-organic framework MIL-53(Al) was synthesized by a solvothermal method using aluminum nitrate as the aluminium source and 1,4-benzenedicarboxylic acid(H2BDC) as the organic ligand. The structure of samples was characterized by X-ray diffraction(XRD) and Fourier transform infrared spectroscopy(FT-IR). The catalytic activity and recyclability of MIL-53(Al) catalyst for the Friedel-Crafts acylation reaction of indole with benzoyl chloride were evaluated. The reaction conditions were optimized and a reaction mechanism was suggested. The results showed that the MIL-53(Al) catalyst exhibited good catalytic activity and recyclability for the Friedel-Crafts acylation reaction. When the molar ratio of indole and MIL-53(Al) catalyst was 1:0.06(n1:ncatalyst), the molar ratio of indole and benzoyl chloride was 1:3, and the solvent was dichloromethane, the conversion of indole could reach 97.1% and the selectivity of 3-acylindole could reach 81.1% at 25 °C after 8 h. The catalyst can be reused without significant degradation in catalytic activity. After the catalyst was reused five times, the conversion of indole was 87.6% and the selectivity of 3-acylindole was 79.5%.Metal-organic framework MIL-53（Al） was synthesized by a solvothermal method using aluminum nitrate as the aluminium source and 1,4-benzenedicarboxylic acid（H2BDC） as the organic ligand. The structure of samples was characterized by X-ray diffraction（XRD） and Fourier transform infrared spectroscopy（FT-IR）. The catalytic activity and recyclability of MIL-53（Al） catalyst for the Friedel-Crafts acylation reaction of indole with benzoyl chloride were evaluated. The reaction conditions were optimized and a reaction mechanism was suggested. The results showed that the MIL-53（Al） catalyst exhibited good catalytic activity and recyclability for the Friedel-Crafts acylation reaction. When the molar ratio of indole and MIL-53（Al） catalyst was 1：0.06（n1：ncatalyst）, the molar ratio of indole and benzoyl chloride was 1：3, and the solvent was dichloromethane, the conversion of indole could reach 97.1% and the selectivity of 3-acylindole could reach 81.1% at 25 °C after 8 h. The catalyst can be reused without significant degradation in catalytic activity. After the catalyst was reused five times, the conversion of indole was 87.6% and the selectivity of 3-acylindole was 79.5%.

关 键 词：MIL-53（Al） CATALYST FRIEDEL-CRAFTS ACYLATION INDOLE 3-acylindoles 

分 类 号：O621.251[理学—有机化学]