Rh(Ⅲ)-Catalyzed sequential ring-retentive/-opening [4+2]annulations of 2H-imidazoles towards full-color emissive imidazo[5,1-a]isoquinolinium salts and AIE-active non-symmetric 1,1-biisoquinolines  

作　　者：Peiyan Zhu Yanyan Yang Hui Li Jinhua Wang Shiqing Li 

机构地区：[1]Guangxi Key Laboratory of Electrochemical and Magneto-Chemical Functional Materials,College of Chemistry and Bioengineering,Guilin University of Technology,Guilin541004,China

出　　处：《Chinese Chemical Letters》2024年第10期213-217,共5页中国化学快报（英文版）

基　　金：financial support from the National Natural Science Foundation of China(Nos.22261013 and 22001049);Guangxi Natural Science Foundation(No.2020GXNSFBA297003);Magneto-Chemical Functional Materials(No.EMFM20221102)。

摘　　要：Rhodium-catalyzed C4aryl-H activation and ring-retentive annulation of 2H-imidazoles with internal alkynes to build imidazo[5,1-a]isoquinolinium salts with high yields and broad scope has been disclosed.These novel salts serve as new full-color emissive fluorophores(433-633 nm),just by simply modifying the substituents on C3 and C4 positions of isoquinoline ring.Furthermore,these salts can undergo ring-opening C5_(aryl)-H activation/annulation with a different alkyne to form non-symmetric and AIE-active1,1-biisoquinolines,where NH_(4)OAc plays an indispensable role that accounts for Hofmann elimination and imine formation,leading to an unprecedented imine dance:cyclic imine→N-alkenyl imine→NH imine.The15N labelling experiments indicate that the 2ndannulation includes two pathways:N-exchange(major)and N-retention(minor).

关 键 词：C-Hactivation/annulation 2H-Imidazole Imidazo[5 1-a]isoquinolinium 1 1'-Biisoquinolines Full-color emission Ring-retentive/-opening 

分 类 号：O626[理学—有机化学]