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Substrate-Selectivity of Strecker Reaction Based on Amino-Functionalized Ga-MIL-53 Catalyst
Author NameAffiliationE-mail
WANG Peng-Cheng College of Chemistry, Jilin University, Changchun 130012, China  
WU Shu-Jie College of Chemistry, Jilin University, Changchun 130012, China  
SHAN Liang College of Chemical and Environmental Engineering, Anyang Institute of Technology, Anyang, Henan 455000, China  
JIANG Yan-Song College of Chemistry, Jilin University, Changchun 130012, China  
FAN Yong College of Chemistry, Jilin University, Changchun 130012, China  
WANG Li College of Chemistry, Jilin University, Changchun 130012, China  
CHEN Xiao-Dong College of Chemistry, Jilin University, Changchun 130012, China  
XU Jia-Ning College of Chemistry, Jilin University, Changchun 130012, China xujn@jlu.edu.cn 
Abstract: This work focuses on Strecker reactions catalyzed by metal-organic framework (MOF) of amino-functionalized Ga-MIL-53 (NH2-Ga-MIL-53) in regard to substrates of a series of N-Ph aldimines, and the results showed that:(1) NH2-Ga-MIL-53 exhibited excellect catalytic activity and good univisality among various substrates; (2) the electronic effect of substituents for substrates primarily affects the catalytic reaction rate, and the electron-donating substituted groups (i.e., MeO, Ph) and electron-withdrawing substituted groups (i.e., CF3, NO2) show promotion and suppression effects on the reaction, respectively; (3) the substituted position of substituents in respect of substrates secondarily influences the reaction rate, and the ortho-substituted MeO group perform the strongest promotion effects on the reaction; (4) as a heterogeneous catalyst, NH2-Ga-MIL-53 can be reused for 9 runs without obvious loss of conversion efficiencies and collapse of MOF structure; (5) contrasting the catalytic performances between NH2-Ga-MIL-53 and Ga-MIL-53, it is indicated that the amino groups of NH2-Ga-MIL-53 can be served as Lewis base moieties, facilating the reaction according to Lewis acid-base synergistic mechanism. Furthermore, comparing the catalytic effects among NH2-Ga-MIL-53, Ga(NO3)3·6H2O and 2-aminoterephthalic acid, it is concluded that the pore structure of NH2-Ga-MIL-53 framework plays a significant role in avoiding the side reactions with respect to Strecker reaction.
Keywords: metal-organic frameworks  gallium  heterogeneous catalysis  Strecker reaction  substrate-selectivity
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WANG Peng-Cheng,WU Shu-Jie,SHAN Liang,JIANG Yan-Song,FAN Yong,WANG Li,CHEN Xiao-Dong,XU Jia-Ning.Substrate-Selectivity of Strecker Reaction Based on Amino-Functionalized Ga-MIL-53 Catalyst[J].Chinese Journal of Inorganic Chemistry,2020,36(3):547-554.
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Chinese Journal of Inorganic Chemistry