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

被引:3
|
作者
Cao, Shuo [1 ]
Chen, Jia-Xin [1 ]
Zhang, Xiu-Li [1 ]
Song, Xian [1 ]
Song, Wen-Yu [1 ]
Wu, Yu-Sheng [1 ]
Zhang, Yan-Hui [2 ]
Liu, Zan [1 ]
机构
[1] Shandong Second Med Univ, Sch Pharm, Weifang 261053, Peoples R China
[2] Shandong Second Med Univ, Sch Med Imaging, Weifang 261053, Peoples R China
关键词
PHOTOREDOX CATALYSIS; H ALKYLATION; METAL; FUNCTIONALIZATION; QUINOXALINONE; HETEROARENES; DERIVATIVES; ARYLATION; HALIDES; BIOMASS;
D O I
10.1021/acs.orglett.4c02021
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reported herein is a practical, economical, and efficient construction of 3-alkylated quinoxalin-2(1H)-ones with alkyl carboxylic acids and alkyl iodides by quinoxalin-2(1H)-one excitation and cobaloxime catalysis. Primary, secondary, and tertiary alkyl iodides and carboxylic acids all could be efficiently transferred into target products with excellent functional group tolerance. Mechanism studies reveal that the quinoxalin-2(1H)-one derivatives could be directly excited and yield alkyl carbon radicals from alkyl carboxylic acids and alkyl iodides with the aid of the cobaloxime complex.
引用
收藏
页码:5833 / 5838
页数:6
相关论文
共 50 条
  • [1] 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
  • [2] Photoinitiated Deaminative Alkylation of Quinoxalin-2(1H)-ones via Electron Catalysis
    Deng, Yangling
    Cheng, Xiya
    Tan, Heping
    He, Yuxuan
    Zhang, Changmei
    Qiu, Guanyinsheng
    Zheng, Danqing
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (06) : 865 - 870
  • [3] 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
  • [4] Electrochemical C3-Fluoroalkoxylation of Quinoxalin-2(1H)-ones with Fluoroalkyl Alcohols for the Synthesis of 3-Fluoroalkoxylated Quinoxalin-2(1H)-ones
    Liu, Yuan-Yuan
    Chen, Lu
    Wang, Ting
    Wang, Guoqin
    Zhang, Minmin
    Jing, Linhai
    Han, Pan
    Zhang, Zheng-Bing
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (34)
  • [5] Metal-free oxidative coupling of quinoxalin-2(1H)-ones with arylaldehydes leading to 3-acylated quinoxalin-2(1H)-ones
    Yuan, Jin-Wei
    Fu, Jun-Hao
    Liu, Shuai-Nan
    Xiao, Yong-Mei
    Mao, Pu
    Qu, Ling-Bo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (17) : 3203 - 3212
  • [6] 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
  • [7] Photoinduced Decarboxylative C3-H Alkylation of Quinoxalin-2(1H)-ones
    Bisoyi, Akash
    Tripathy, Alisha Rani
    Yedase, Girish Suresh
    Sinu, P. Shifana
    Choudhury, Udita
    Yatham, Veera Reddy
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04) : 2631 - 2641
  • [8] Transition-metal free direct C-H functionalization of quinoxalin-2(1H)-ones with oxamic acids leading to 3-carbamoyl quinoxalin-2(1H)-ones
    Yuan, Jin-Wei
    Zhu, Jun-Liang
    Zhu, Hu-Lin
    Peng, Fang
    Yang, Liang-Yu
    Mao, Pu
    Zhang, Shou-Ren
    Li, Yan-Chun
    Qu, Ling-Bo
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (02): : 273 - 285
  • [9] Copper-catalyzed oxidative coupling of quinoxalin-2(1H)-ones with alcohols: access to hydroxyalkylation of quinoxalin-2(1H)-ones
    Fu, Junhao
    Yuan, Jinwei
    Zhang, Yue
    Xiao, Yongmei
    Mao, Pu
    Diao, Xiaoqiong
    Qu, Lingbo
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (23): : 3382 - 3390
  • [10] 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