Light-Induced Difunctionalization of Alkenes with Polyhaloalkanes and Quinoxalin-2(1H)-ones

被引:1
|
作者
Kumar, Vivek [1 ]
Bisoyi, Akash [1 ]
Beevi, V. Fathima [1 ]
Yatham, Veera Reddy [1 ]
机构
[1] Indian Inst Sci Educ & Res, Sch Chem, Thiruvananthapuram 695551, Kerala, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 22期
关键词
ALKYL-HALIDES; 1,4-ADDITION; RADICALS; TMSCCL3; AMINES;
D O I
10.1021/acs.joc.4c02119
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report a metal-free light-induced three-component reaction for the synthesis of polychloroalkyl-substituted quinoxalin-2(1H)-ones using commercially available alkenes, polyhalo alkanes, and quinoxalin-2(1H)-ones. Preliminary mechanistic studies suggested the generation of radical intermediates via an EDA-complex, single electron transfer, or halogen atom transfer pathway. Under mild reaction conditions, various alkenes and quinoxalin-2(1H)-ones containing different functional groups are compatible, providing the corresponding polychloroalkyl-substituted quinoxalin-2(1H)-ones in moderate to good yields.
引用
收藏
页码:16964 / 16968
页数:5
相关论文
共 50 条
  • [21] Ammonium Persulfate Promotes Trifluoromethylation of Quinoxalin-2(1H)-ones
    Yi, Rongnan
    Liu, Dongxian
    He, Jiangnan
    Zhao, Mingming
    Xu, Xinhua
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (08) : 3285 - 3291
  • [22] Visible-Light-Induced Alkoxylation of Quinoxalin-2(1H)-ones with Alcohols for the Synthesis of Heteroaryl Ethers
    Zhao, Lulu
    Wang, Lei
    Gao, Yanhui
    Wang, Zhiming
    Li, Pinhua
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (23) : 5363 - 5370
  • [23] 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
  • [24] Photo-/electrocatalytic functionalization of quinoxalin-2(1H)-ones
    Sun, Kai
    Xiao, Fang
    Yu, Bing
    He, Wei-Min
    CHINESE JOURNAL OF CATALYSIS, 2021, 42 (11) : 1921 - 1943
  • [25] Phenyliodonium Diacetate Mediated Carbotrifluoromethylation of Quinoxalin-2(1H)-ones
    Xue, Wenxuan
    Su, Yingpeng
    Wang, Ke-Hu
    Cao, Lindan
    Feng, Yawei
    Zhang, Weigang
    Huang, Danfeng
    Hu, Yulai
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (06) : 887 - 892
  • [26] Visible-light-induced C-H arylation of quinoxalin-2(1H)-ones in H2O
    Bao, Hanyang
    Lin, Ziyun
    Jin, Mengshi
    Zhang, Hongdou
    Xu, Jun
    Chen, Bajin
    Li, Wanmei
    TETRAHEDRON LETTERS, 2021, 66
  • [27] Electrochemical Hydroalkylation of Quinoxalin-2(1H)-ones with Alkyl Halides
    Qiu, Zhihong
    Huang, Xianting
    Wu, Jintao
    Liu, Zhong-Quan
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (03) : 318 - 322
  • [28] Direct C(sp2)-H fluoroalkylation of quinoxalin-2(1H)-ones with (fluoroalkyl)triphenylphosphonium salts and alkenes
    Wang, Wenwen
    Zhu, Tonghao
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (21) : 5375 - 5382
  • [29] Visible Light-Induced Radical Cyclization of Ethyl 2-(N-Arylcarbamoyl)-2-Chloroiminoacetates: Synthesis of Quinoxalin-2(1H)-ones
    Li, Dianjun
    Ma, Haichao
    Ye, Wei
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (16-17) : 3696 - 3702
  • [30] Photocatalyst-free visible light induced decarboxylative alkylation of quinoxalin-2(1H)-ones with carboxylic acids
    Hong, Yun-Yun
    Peng, Zhen
    Ma, Hui
    Zhu, Qi
    Xu, Xiang-Qin
    Yang, Li-Hua
    Xie, Long-Yong
    TETRAHEDRON LETTERS, 2022, 89