Visible Light-Induced Electron-Donor-Acceptor-Mediated C-3 Coupling of Quinoxalin-2(1H)-ones with Unactivated Aryl Iodides

被引:4
|
作者
Singh, Nihal [1 ]
Sharma, Anoop [1 ]
Singh, Jitender [1 ]
Pandey, Amar Prakash [1 ]
Sharma, Anuj [1 ]
机构
[1] Indian Inst Technol Roorkee, Dept Chem, Roorkee 247667, Uttarakhand, India
关键词
C-H ARYLATION; DECARBOXYLATIVE ACYLATION; ACYL PEROXIDES; METAL; QUINOXALINONES; PHOTOCATALYST; SALTS; QUINOXALIN-2(H)-ONES; 3-ARYLATION; AMINATION;
D O I
10.1021/acs.orglett.4c02296
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Visible light-induced C-3 arylation of quinoxalin-2(1H)-ones with abundantly available aryl iodides with good yields via an electron-donor-acceptor (EDA)-complex formation have been accomplished. The radical scavenging, Electron paramagnetic resonance (EPR), UV-visible experiments, density functional theory (DFT), and quantum yield studies revealed that the reaction went through a radical pathway via a single electron transfer (SET) process. Furthermore, the protocol could also be applied to the synthesis of biologically active molecules, illustrating the practicality of the present protocol.
引用
收藏
页码:6471 / 6476
页数:6
相关论文
共 50 条
  • [1] Visible-Light Mediated C-3 Amination of Quinoxalin-2(1H)-ones via Electron Donor-Acceptor Complexation
    More, Devidas A.
    Gayathri, P. R.
    Thete, Kishor R.
    Muthukrishnan, M.
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (08)
  • [2] Merging Quinoxalin-2(1H)-ones Excitation with Cobaloxime Catalysis: C3 Alkylation of Quinoxalin-2(1H)-ones with Unactivated Alkyl Iodides and Carboxylic Acids under Light
    Cao, Shuo
    Chen, Jia-Xin
    Zhang, Xiu-Li
    Song, Xian
    Song, Wen-Yu
    Wu, Yu-Sheng
    Zhang, Yan-Hui
    Liu, Zan
    ORGANIC LETTERS, 2024, : 5833 - 5838
  • [3] Visible-Light-Mediated C3-H Acetalation of Quinoxalin-2(1H)-ones
    Zhang Mengqi
    Nan Guangming
    Zhao Xiaohui
    Wei Wei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) : 4315 - 4322
  • [4] Zwitterions as catalytic electron donor species for visible light-induced photoactivation of oxime esters and direct C3-alkylation of quinoxalin-2(1H)-ones
    Mao, Haichen
    Zhang, Yuting
    Cao, Hengrong
    Chang, Junbiao
    Zhu, Bo
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (23): : 6784 - 6789
  • [5] Light-Induced Difunctionalization of Alkenes with Polyhaloalkanes and Quinoxalin-2(1H)-ones
    Kumar, Vivek
    Bisoyi, Akash
    Beevi, V. Fathima
    Yatham, Veera Reddy
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (22): : 16964 - 16968
  • [6] Merging Visible-Light Photoredox and Organoamine Catalysis for the C-3 Difluoroalkylation of Quinoxalin-2(1H)-Ones
    Jin, Can
    Zhuang, Xiaohui
    Sun, Bin
    Li, Deyu
    Zhu, Rui
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (08) : 1490 - 1494
  • [7] Metal-free visible-light-initiated direct C3 alkylation of quinoxalin-2(1H)-ones and coumarins with unactivated alkyl iodides
    Sun, Jun
    Yang, Hua
    Zhang, Bo
    GREEN CHEMISTRY, 2022, 24 (02) : 858 - 863
  • [8] Visible-Light-Induced Direct C-H Amination of Quinoxalin-2(1H)-ones
    Liu, Yanpeng
    Pei, Congcong
    Chen, Xiaoyu
    Zhang, Jianye
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (05) : 709 - 714
  • [9] Photocatalyst-Free Visible Light-Induced C(sp2)-H Arylation of Quinoxalin-2(1H)-ones and Coumarins
    Yu, Dingzhe
    Yang, Wenjing
    Chen, Shuicai
    Zhou, Cong-Ying
    Guo, Zhen
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (44)
  • [10] Visible-light induced decarboxylative alkylation of quinoxalin-2(1H)-ones at the C3-position
    Xue, Wenxuan
    Su, Yingpeng
    Wang, Ke-Hu
    Zhang, Rong
    Feng, Yawei
    Cao, Lindan
    Huang, Dangfeng
    Hu, Yulai
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (27) : 6654 - 6661