Organic photoredox catalyzed C-H silylation of quinoxalinones or electron-deficient heteroarenes under ambient air conditions

被引:75
|
作者
Dai, Changhui [1 ]
Zhan, Yanling [1 ]
Liu, Ping [1 ]
Sun, Peipei [1 ]
机构
[1] Nanjing Normal Univ, Jiangsu Collaborat Innovat Ctr Biomed Funct Mat, Sch Chem & Mat Sci, Jiangsu Prov Key Lab Mat Cycle Proc & Pollut Cont, Nanjing 210023, Peoples R China
基金
中国国家自然科学基金;
关键词
BOND SILYLATION; FACILE ACCESS; ALKENES; ARENES; MOLECULES; SILANES; ESTERS; ROUTE;
D O I
10.1039/d0gc03697h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Direct C-H silylation of quinoxalinones was achieved by the combination of organic photoredox catalysis and hydrogen atom transfer (HAT) under ambient air conditions. Transition metal- and external oxidant-free conditions were the major features of this protocol. A series of silylated quinoxalinones with broad functional groups had been synthesized in moderate to high yields. This methodology was also applicable for the C-H silylation of some electron-deficient heteroarenes.
引用
收藏
页码:314 / 319
页数:6
相关论文
共 50 条
  • [1] Research of Quinuclidine-Promoted C-H Silylation of Electron-Deficient Nitrogen Heteroarenes
    Pan Peng
    Yuan Qiyang
    Liu Shihue
    Zhao Jianhong
    Zhang Yongqiang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (04) : 1136 - 1145
  • [2] Photoredox catalyzed C-H trifluoroethylamination of heteroarenes
    Wang, Juan
    Liu, Shuai
    Huang, Yangen
    Xu, Xiu-Hua
    Qing, Feng-Ling
    CHEMICAL COMMUNICATIONS, 2022, 58 (09) : 1346 - 1349
  • [3] Transition-Metal-Free Direct C-H Silylation of Electron-Deficient Heteroarenes with Hydrosilanes via a Radical Mechanism
    Sakamoto, Ryu
    Nguyen, Bich-Ngoc
    Maruoka, Keiji
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (06) : 1085 - 1088
  • [4] Photoredox-Catalyzed Decarboxylative C-H Acylation of Heteroarenes
    Jia, Wei
    Jian, Yong
    Huang, Binbin
    Yang, Chao
    Xia, Wujiong
    SYNLETT, 2018, 29 (14) : 1881 - 1886
  • [5] Photoredox-catalyzed direct C-H monofluoromethylation of heteroarenes
    Ramkumar, Nagarajan
    Plantus, Ketrina
    Ozola, Melita
    Mishnev, Anatoly
    Nikolajeva, Vizma
    Senkovs, Maris
    Oseka, Maksim
    Veliks, Janis
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (44) : 20642 - 20652
  • [6] Efficient iridium-catalyzed C-H functionalization/silylation of heteroarenes
    Lu, Biao
    Falck, John R.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) : 7508 - 7510
  • [7] Rhodium(II)-Catalyzed C-H Functionalization of Electron-Deficient Methyl Groups
    Fu, Liangbing
    Guptill, David M.
    Davies, Huw M. L.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (18) : 5761 - 5764
  • [8] Nickel-catalyzed regioselective C-H halogenation of electron-deficient arenes
    Li, Ze-Lin
    Wu, Peng-Yu
    Cai, Chun
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (08) : 3462 - 3468
  • [9] Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: Scope, tunability, and predictability
    Blackmond, D.G. (blackmond@scripps.edu), 1600, American Chemical Society (135):
  • [10] Unusual Regioselective C-H Difluoroalkylation of Heteroarenes under Photoredox Catalysis
    Laru, Sudip
    Ghoshal, Sourav
    Sarkar, Pranab
    Hajra, Alakananda
    ORGANIC LETTERS, 2024, 26 (24) : 5098 - 5104