Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes

被引：29
|
作者：
Kuribara, Takahito [1 ]
Nakajima, Masaya [1 ]
Nemoto, Tetsuhiro [1 ]
机构：
[1] Chiba Univ, Grad Sch Pharmaceut Sci, Chuo Ku, Chiba 2608675, Japan
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 06期
关键词：
AB-INITIO PSEUDOPOTENTIALS; DIRECT AMIDATION; AMINATION; HETEROARENES; PRECURSORS; RADICALS; 2ND;
D O I：
10.1021/acs.orglett.0c00433
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation
引用
收藏
页码：2235 / 2239
页数：5
相关论文
共 50 条
  • [1] Metal- and photocatalyst-free approach to visible-light-induced acylation of quinoxalinones
    Niwetmarin, Worawat
    Saesian, Naiyana
    Saruengkhanphasit, Rungroj
    Eurtivong, Chatchakorn
    Thasana, Nopporn
    Ruchirawat, Somsak
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (29) : 5924 - 5929
  • [2] 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,
  • [3] Direct C-H sulfenylation of quinoxalinones with thiols under visible-light-induced photocatalyst-free conditions
    Teng, Qing-Hu
    Yao, Yan
    Wei, Wen-Xiu
    Tang, Hai-Tao
    Li, Jia-Rong
    Pan, Ying-Ming
    GREEN CHEMISTRY, 2019, 21 (23) : 6241 - 6245
  • [4] Visible-Light-Induced Metal- and Photocatalyst-Free Radical Cascade Cyclization of Cinnamamides for Synthesis of Functionalized Dihydroquinolinones
    Nishad, Chandra Shekhar
    Suman, Pallav
    Saha, Himadri
    Banerjee, Biplab
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15): : 11010 - 11022
  • [5] Visible-Light-Induced Photocatalyst-Free Radical Trifluoromethylation
    Li, Yufei
    Liang, Xin
    Niu, Kaikai
    Gu, Jun
    Liu, Fang
    Xia, Qing
    Wang, Qingmin
    Zhang, Weihua
    ORGANIC LETTERS, 2022, 24 (32) : 5918 - 5923
  • [6] Visible Light Promoted Metal- and Photocatalyst-Free Synthesis of Allylarenes
    Dossena, Alessandro
    Sampaolesi, Susanna
    Palmieri, Alessandro
    Protti, Stefano
    Fagnoni, Maurizio
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19): : 10687 - 10692
  • [7] 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
  • [8] Metal- and photocatalyst-free visible-light-promoted regioselective selenylation of coumarin derivatives via oxidation-induced C-H functionalization
    Yang, Daoshan
    Li, Guoqing
    Xing, Chengyu
    Cui, Wenwen
    Li, Kexin
    Wei, Wei
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (20): : 2974 - 2979
  • [9] 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
  • [10] Visible-light-induced photocatalyst-free dearomative amidation of phenol derivatives
    Wu, Lingang
    Sun, Lei
    Liu, Wanxing
    Cui, Jichun
    Xie, Lei
    TETRAHEDRON LETTERS, 2023, 128
12345