首页|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

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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Photocatalytic and photoinduced silyl radicals cascade cyclization procedures for the green and sim-ple 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*[E1/2(*P/P-)=+1.97 V vs.SCE in MeCN]by 3-acetoxyquinuclidine(Ep=+1.22 V vs.SCE in MeCN),and(2)the thermodynamic feasibil-ity 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.

Indolo[2,1-a]isoquinolinesSilyl radicalsGreen photocatalyticSimple photoinducedSilylatedHydrogen atom transferEDA complex

Zhenkai Lei、Fei Xue、Bin Wang、Shijie Wang、Yu Xia、Yonghong Zhang、Weiwei Jin、Chenjiang Liu

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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

Xinjiang Uygur Autonomous Region Product Quality Supervision and Inspection Institute,Urumqi 830011,China

College of Future Technology,Institute of Materia Medica,Xinjiang University,Urumqi 830017,China

Tianshan Talents Program for Leading Talents in Science and Technology Innovation国家自然科学基金国家自然科学基金Program for Tianshan Innovative Research Team of Xinjiang Uygur Autonomous RegionGraduate Innovation Project of Xinjiang Uygur Autonomous RegionKey Program of Natural Science Foundation of Xinjiang Uygur Autonomous Region新疆维吾尔自治区自然科学基金新疆维吾尔自治区自然科学基金

2022TSYCLJ001621961037222012412021D14011XJ2021G0362022D01D062021D01E102022E01042

2024

10.1016/j.cclet.2023.108633

中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

CSTPCD
影响因子：0.771
ISSN：1001-8417
年,卷(期)：2024.35(1)
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