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

Zhenkai Lei ¹Fei Xue ²Bin Wang ²Shijie Wang ²Yu Xia ²Yonghong Zhang ²Weiwei Jin ²Chenjiang Liu³

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作者信息

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;Xinjiang Uygur Autonomous Region Product Quality Supervision and Inspection Institute,Urumqi 830011,China
2. 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
3. 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;College of Future Technology,Institute of Materia Medica,Xinjiang University,Urumqi 830017,China
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Abstract

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.

Key words

Indolo[2,1-a]isoquinolines/Silyl radicals/Green photocatalytic/Simple photoinduced/Silylated/Hydrogen atom transfer/EDA complex

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基金项目

Tianshan Talents Program for Leading Talents in Science and Technology Innovation(2022TSYCLJ0016)

国家自然科学基金(21961037)

国家自然科学基金(22201241)

Program for Tianshan Innovative Research Team of Xinjiang Uygur Autonomous Region(2021D14011)

Graduate Innovation Project of Xinjiang Uygur Autonomous Region(XJ2021G036)

Key Program of Natural Science Foundation of Xinjiang Uygur Autonomous Region(2022D01D06)

新疆维吾尔自治区自然科学基金(2021D01E10)

新疆维吾尔自治区自然科学基金(2022E01042)

出版年

2024

中国化学快报(英文版)

中国化学会

中国化学快报(英文版)

CSTPCDCSCD

影响因子：0.771

ISSN：1001-8417

参考文献量84

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