Radical cascade cyclization for the green and simple synthesis of silylated indolo[2,1-a]isoquinoline derivatives via visible light-mediated Si–H bonds activation  

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作  者:Zhenkai Lei Fei Xue Bin Wang Shijie Wang Yu Xia Yonghong Zhang Weiwei Jin Chenjiang Liu 

机构地区:[1]State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources,Key Laboratory of Oil and Gas Fine Chemicals,Ministry of Education&Xinjiang Uygur Autonomous Region,Urumqi Key Laboratory of Green Catalysis and Synthesis Technology,College of Chemistry,Xinjiang University,Urumqi 830017,China [2]College of Future Technology,Institute of Materia Medic1,Xinjiang University,Urumqi 830017,China [3]Xinjiang Uygur Autonomous Region Product Quality Supervision and Inspection Institute,Urumqi 830011,China

出  处:《Chinese Chemical Letters》2024年第1期243-249,共7页中国化学快报(英文版)

基  金:the Tianshan Talents Program for Leading Talents in Science and Technology Innovation(No.2022TSYCLJ0016);the National Natural Science Foundation of China(Nos.21961037 and 22201241);the Program for Tianshan Innovative Research Team of Xinjiang Uygur Autonomous Region(No.2021D14011);the Graduate Innovation Project of Xinjiang Uygur Autonomous Region(No.XJ2021G036);the Key Program of Natural Science Foundation of Xinjiang Uygur Autonomous Region(No.2022D01D06);the Natural Science Foundation of Xinjiang Uygur Autonomous Region(Nos.2021D01E10 and 2022E01042).

摘  要:Photocatalytic and photoinduced silyl radicals cascade cyclization procedures for the green and simple preparation of fused tetracyclic skeleton silylated indolo[2,1-a]isoquinoline-6(5H)-ones from 2-aryl-N-acryloyl indoles with hydrosilanes are developed.The photocatalytic reaction is carried out with 9,10-dicyanoanthracene(DCA)as an organophotocatalyst and 3-acetoxyquinuclidine as hydrogen atom transfer(HAT)catalyst at room temperature under metal-and oxidant-free conditions.The keys to the success of photoredox-catalytic conversion include(1)the reductive quenching of DCA^(*)[E_(1/2)(*P/P^(-))=+1.97 V vs.SCE in MeCN]by 3-acetoxyquinuclidine(E_(p)=+1.22 V vs.SCE in MeCN),and(2)the thermodynamic feasibility of hydrogen atom abstraction from hydridic Si-H bond by electrophilic N^(+·).Particularly,the simple photoinduced cascade cyclization using(TMS)3SiH with 2-aryl-N-acryloyl indoles was exploited via an electron-donor-acceptor(EDA)complex under visible light irradiation.

关 键 词:Indolo[2 1-a]isoquinolines Silyl radicals Green photocatalytic Simple photoinduced Silylated Hydrogen atom transfer EDA complex 

分 类 号:O626[理学—有机化学]

 

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