Photocatalyst-Free Regioselective C-H Thiocyanation of 4-Anilinocoumarins under Visible Light

被引:97
作者
Li, Guoqing [2 ]
Yan, Qiuli [1 ,2 ]
Gong, Xueqin [2 ]
Dou, Xiaomeng [3 ]
Yang, Daoshan [1 ,2 ]
机构
[1] Qingdao Univ Sci & Technol, Coll Chem & Mol Engn, State Key Lab Base Ecochem Engn, Zhengzhou Rd 53, Qingdao 266042, Shandong, Peoples R China
[2] Qufu Normal Univ, Sch Chem & Chem Engn, Yulong Rd 57, Qufu 273165, Peoples R China
[3] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Taoyuan Rd 1, Xiangtan 411201, Peoples R China
来源
ACS SUSTAINABLE CHEMISTRY & ENGINEERING | 2019年 / 7卷 / 16期
基金
中国国家自然科学基金;
关键词
Photocatalyst-free; C-H thiocyanation; Visible light; Enaminone; Sustainable synthetic chemistry; QUINOLINE N-OXIDES; PHOTOREDOX CATALYSIS; BOND FUNCTIONALIZATION; AMMONIUM THIOCYANATE; C-3; THIOCYANATION; INDOLES; ACTIVATION; COUMARINS; DERIVATIVES; ALKYLATION;
D O I
10.1021/acssuschemeng.9b02511
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the present study, we describe the successful development of a novel and efficient C(sp(2))-H thiocyanation reaction of electron-rich heteroarenes and arenes with readily available ammonium thiocyanate under visible light exposure. Most importantly, the reaction proceeded smoothly without addition of any photocatalyst or strong oxidant, ultimately minimizing the production of chemical waste. The advantages of this reaction met the requirements of green and sustainable synthetic chemistry and may be widely used in organic synthesis and pharmaceutical chemistry.
引用
收藏
页码:14009 / 14015
页数:13
相关论文
共 50 条
  • [1] External photocatalyst-free C-H alkylation of N- sulfonyl ketimines with alkanes under visible light
    Song, Hai-Yang
    Xiao, Fang
    Jiang, Jun
    Wu, Chao
    Ji, Hong -Tao
    Lu, Yu-Han
    Wang, Ke-Li
    He, Wei-Min
    CHINESE CHEMICAL LETTERS, 2023, 34 (09)
  • [2] Photocatalyst-Free, Visible-Light-Mediated C-H Perfluoroalkylation of Quinazolin-4(3 H )-ones with perfluoroalkyl Iodides
    Delouche, Thomas
    Gadiry-Diallo, Abdoul
    Besson, Thierry
    Ogoshi, Sensuke
    Fruit, Corinne
    SYNTHESIS-STUTTGART, 2023, 55 (21): : 3670 - 3684
  • [3] Photocatalyst-Free Visible-Light-Promoted C-3-Alkylation of Indoles through C-H Functionalizations of N,N-Dialkylanilines
    Saikia, B. Shriya
    Deb, Mohit L.
    Baruah, Pranjal K.
    CHEMISTRYSELECT, 2023, 8 (37):
  • [4] Visible light-promoted photocatalyst-free activation of persulfates: a promising strategy for C-H functionalization reactions
    Saha, Sudipta
    Bagdi, Avik Kumar
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (16) : 3249 - 3262
  • [5] Photocatalyst-Free Visible-Light-Promoted C-H Selenylation of Pyrazolo[1,5-a ]pyrimidines
    Sikdar, Papiya
    Choudhuri, Tathagata
    Paul, Suvam
    Das, Sourav
    Kumar, Anil
    Bagdi, Avik Kumar
    SYNTHESIS-STUTTGART, 2023, 55 (21): : 3693 - 3699
  • [6] Recent Advances in Visible-Light-Induced C(3)-H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free
    Dong, Jianghu
    Xuan, Liangming
    Wang, Chi
    Zhao, Chenxi
    Wang, Haifeng
    Yan, Qiongjiao
    Wang, Wei
    Chen, Fen'er
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (01) : 111 - 136
  • [7] Harnessing Visible/UV Light for the Activation and/or Functionalization of C-H Bonds: Metal- and Photocatalyst-Free Approach
    Bariwal, Jitender
    van der Eycken, Erik
    CHEMICAL RECORD, 2025,
  • [8] Visible-light-induced photocatalyst-free intramolecular sp3 C-H oxidation of 2 alkyl benzamides
    Wu, Lingang
    Sun, Lei
    Cui, Jichun
    Xie, Lei
    Wang, Yanlan
    Nie, Shaozhen
    TETRAHEDRON LETTERS, 2022, 107
  • [9] Visible-light-promoted aerobic oxidative synthesis of β-ketosulfones under photocatalyst-free conditions
    Lv, Yufen
    Liu, Qishun
    Liu, Fei
    Yue, Huilan
    Li, Jiang-Sheng
    Wei, Wei
    TETRAHEDRON LETTERS, 2020, 61 (01)
  • [10] Transition-metal-free KI-catalyzed regioselective sulfenylation of 4-anilinocoumarins using Bunte salts
    Li, Guoqing
    Zhang, Guomeng
    Deng, Xuewu
    Qu, Kunyu
    Wang, Hua
    Wei, Wei
    Yang, Daoshan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (43) : 8015 - 8019