Metal-Free Direct C3-H Alkylation and Arylation of Quinoxalin-2(1H)-Ones with Inert Alkyl and Aryl Chlorides

被引:8
|
作者
Tripathy, Alisha Rani [1 ]
Mishra, Ashutosh [1 ]
Singh, Vesaj [1 ]
Yatham, Veera Reddy [1 ]
机构
[1] Indian Inst Sci Educ & Res, Sch Chem, Thiruvananthapuram IISER TVM, Thiruvananthapuram 695551, India
关键词
alkyl chlorides; halo arenes; organo photocatalyst; quinoxalin-2(1H)-ones; visible-light; LATE-STAGE FUNCTIONALIZATION; PHOTOREDOX CATALYSIS; CHLORINATION; HALIDES; OLEFINS;
D O I
10.1002/chem.202300774
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the present manuscript, we reported the first visible-light-enabled direct C3-H alkylation/arylation of quinoxalin-2(1H)-ones with unactivated alkyl/aryl chlorides under metal-free conditions. A wide range of unactivated alkyl and aryl chlorides containing different functionalities are coupled with a variety of quinoxalin-2(1H)-one derivatives under mild reaction conditions to afford the C3-alkyl/aryl substituted quinoxalin-2(1H)-ones in moderate to good yields.
引用
收藏
页数:6
相关论文
共 50 条
  • [31] Eosin Y as a direct hydrogen-atom transfer photocatalyst for the C3-H acylation of quinoxalin-2(1H)-ones
    Ni, Hangcheng
    Li, Yu
    Shi, Xingzi
    Pang, Yi
    Jin, Congying
    Zhao, Fei
    TETRAHEDRON LETTERS, 2021, 68
  • [32] Metal-Free Trifluoroalkylation of Quinoxalin-2(1H)-ones with Unactivated Alkenes and Langlois' Reagent
    Meng, Na
    Wang, Leilei
    Liu, Qishun
    Li, Qinyu
    Lv, Yufen
    Yue, Huilan
    Wang, Xiaojuan
    Wei, Wei
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (11): : 6888 - 6896
  • [33] Transition Metal-Free Iodosobenzene-Promoted Direct Oxidative 3-Arylation of Quinoxalin-2(H)-ones with Arylhydrazines
    Paul, Sanjay
    Ha, Ji Hyeon
    Park, Ga Eul
    Lee, Yong Rok
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (09) : 1515 - 1521
  • [34] Recent Advances in Visible-Light-Enabled C3-H Fluoroalkylation of Quinoxalin-2(1H)-ones
    Ma, Dong
    Wu, Xinfen
    Xiao, Tiebo
    CHEMISTRYSELECT, 2025, 10 (12):
  • [35] Direct C-H Arylation of Quinoxalin-2(H)-ones with Arylhydrazine hydrochlorides
    Liang, Yue-Pei
    He, Ya-Nan
    Jiang, Ze-Qun
    Yang, Li-Hua
    Xie, Long-Yong
    CHEMISTRYSELECT, 2023, 8 (05):
  • [36] Photocatalyst-, metal- and additive-free, direct C-H arylation of quinoxalin-2(1H)-ones with aryl acyl peroxides induced by visible light
    Xu, Jun
    Zhang, Hongdou
    Zhao, Jianming
    Ni, Zhigang
    Zhang, Pengfei
    Shi, Bing-Feng
    Li, Wanmei
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (24) : 4031 - 4042
  • [37] Direct C-H Trifluoromethylation of Quinoxalin-2(1H)-ones under Transition-Metal-Free Conditions
    Wang, Liping
    Zhang, Yuecheng
    Li, Fanfan
    Hao, Xinyu
    Zhang, Hong-Yu
    Zhao, Jiquan
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (20) : 3969 - 3977
  • [38] Direct electrochemical C-3 arylation of Quinoxalin-2(1H)- ones with cyanoaromatics via paired electrolysis
    Deng, Yang
    Wang, Xiao-Wen
    Lv, Jin-Feng
    Guan, Zhi
    He, Yan-Hong
    TETRAHEDRON, 2024, 153
  • [39] Transition metal-free C-3 functionalization of quinoxalin-2(1H)-ones: recent advances and sanguine future
    Kiran
    Rani, Payal
    Chahal, Sandhya
    Sindhu, Jayant
    Kumar, Sudhir
    Varma, Rajender S.
    Singh, Rajvir
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (40) : 18722 - 18763
  • [40] Metal-free regioselective nitration of quinoxalin-2(1H)-ones with tert-butyl nitrite
    Li, Yi-Na
    Li, Xue-Lin
    Wu, Jin-Bo
    Jiang, Hong
    Liu, Yunmei
    Guo, Yu
    Zeng, Yao-Fu
    Wang, Zhen
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (48) : 10554 - 10559