Application of HSAB Theory in the Selective Reduction of Quinoline  

作　　者：Tianwei Liu Jianghua He Yuetao Zhang 

机构地区：[1]State Key Laboratory of Supramolecular Structure and Materials,College of Chemistry,Jilin University,Changchun,Jilin,130012 China

出　　处：《Chinese Journal of Chemistry》2023年第19期2446-2452,共7页中国化学（英文版）

基　　金：supported by the National Natural Science Foundation of China(Grant Nos.21871107,22225104,21975102,22071077).

摘　　要：It is very important to develop efficient synthetic strategies for site-specific functionalization of tetrahydroquinolines due to their indispensable roles in pharmaceutical and agrochemical industries.We apply hard/soft acid/base(HSAB)theory to selective reduction of quinoline and achieve a series of C3-functionalized tetrahydroquinoline in high to excellent yields(up to 99%)under mild conditions with the catalysis of B(C_(6)F_(5))_(3).A series of in situ NMR reactions are also performed to investigate this cascade reaction.Moreover,AB type monomer 6-(dimethylsilyl)quinoline and AA/BB type monomer 6,6'-biquinoline are synthesized for polymer synthesis,which represents the first example of silicon bridged polytetrahydroquinoline.

关 键 词：HYDROBORATION HYDROSILYLATION Organocatalysis Quinoline REDUCTION SELECTIVITY 

分 类 号：O62[理学—有机化学]