Visible-Light Promoted Catalyst-Free Imidation of Arenes and Heteroarenes

被引:124
|
作者
Song, Lu [1 ]
Zhang, Long [1 ]
Luo, Sanzhong [1 ,2 ]
Cheng, Jin-Pei [1 ]
机构
[1] Chinese Acad Sci Beijing, BNLMS, CAS Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
关键词
CH imidation; N-bromosaccharin; photolysis; visible-light; C-H AMINATION; N BOND FORMATION; INTERMOLECULAR AMINATION; IMIDYL RADICALS; TRIFLUOROMETHYLATION; AMIDATION; ROUTE; MILD; FUNCTIONALIZATION; PHTHALIMIDATION;
D O I
10.1002/chem.201404479
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We described herein a catalyst-free visible-light photolytic protocol for the imidation of arenes and heteroarenes. N-Bromosaccharin was identified as a viable and chemoselective nitrogen radical precursor that undergoes controllable homolytic cleavage under ambient light irradiation. The reaction can be applied to a number of arenes and heteroarenes with good chemo- and regioselectivity. Mechanistic studies revealed that radical chain termination by electron transfer-proton transfer (ET-PT) is the leading productive pathway for the reaction.
引用
收藏
页码:14231 / 14234
页数:4
相关论文
共 50 条
  • [21] Catalyst-Free Visible Light-Induced RAFT Photopolymerization
    Xu, Jiangtao
    Shanmugam, Sivaprakash
    Corrigan, Nathaniel Alan
    Boyer, Cyrille
    CONTROLLED RADICAL POLYMERIZATION, VOL 1: MECHANISMS, 2015, 1187 : 247 - +
  • [22] Quinone-Mediated Trifluoromethylation of Arenes and Heteroarenes with Visible Light
    Chang, Bin
    Shao, Hongge
    Yan, Peng
    Qiu, Wenzhao
    Weng, Zhigiang
    Yuan, Rusheng
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (01): : 334 - 341
  • [23] Catalyst-free, visible-light-promoted S-H insertion reaction between thiols and α-diazoesters
    Yang, Jingya
    Wang, Ganggang
    Chen, Shuwen
    Ma, Ben
    Zhou, Hongyan
    Song, Menghui
    Liu, Cai
    Huo, Congde
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (46) : 9494 - 9498
  • [24] VISIBLE LIGHT PROMOTED CATALYST-FREE GREEN SYNTHESIS OF 1,3,5-TRIARYLPYRAZOLES IN AQUEOUS MEDIUM
    Siddiqui, A.
    Sinha, A.
    Tripathi, V.
    Yadav, A.
    Singh, G.
    Kumar, G.
    Fatima, N.
    Saquib, Mohammad
    Bhadauria, V.
    HETEROCYCLIC LETTERS, 2025, 15 (01): : 157 - 165
  • [25] Visible-light mediated carbamoyl radical addition to heteroarenes
    Jatoi, Ashique Hussain
    Pawar, Govind Goroba
    Robert, Frederic
    Landais, Yannick
    CHEMICAL COMMUNICATIONS, 2019, 55 (04) : 466 - 469
  • [26] Direct C-H Phosphonylation of Electron-Rich Arenes and Heteroarenes by Visible-Light Photoredox Catalysis
    Shaikh, Rizwan S.
    Ghosh, Indrajit
    Koenig, Burkhard
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (50) : 12120 - 12124
  • [27] Catalyst and Sensitizer-Free Visible-Light-Induced C(sp2)-H Chalcogenation of Arenes/Heteroarenes with Dichalcogenides
    Kumaraswamy, Gullapalli
    Ramesh, Vankudoth
    Gangadhar, Maram
    Vijaykumar, Swargam
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (08) : 1689 - 1697
  • [28] Organic Dye-Catalyzed, Visible-Light Photoredox Bromination of Arenes and Heteroarenes Using N-Bromosuccinimide
    Roger, David A.
    Brown, Roxanne G.
    Brandeburg, Zachary C.
    Ko, Eric Y.
    Hopkins, Megan D.
    LeBlanc, Gabriel
    Lamar, Angus A.
    ACS OMEGA, 2018, 3 (10): : 12868 - 12877
  • [29] Visible-light promoted bimetallic catalysis
    Inagaki, Akiko
    Akita, Munetaka
    COORDINATION CHEMISTRY REVIEWS, 2010, 254 (11-12) : 1220 - 1239
  • [30] Novel catalyst-free activation of chlorine by visible light for micropollutant abatement
    Zeng, Ge
    An, Linqian
    Jiang, Maoju
    Li, Wenqi
    Hou, Xiangyang
    Su, Peng
    Liu, Minchao
    Cheng, Haijun
    Long, Zhiyun
    Yang, Jingxin
    Ma, Jun
    Yang, Tao
    JOURNAL OF HAZARDOUS MATERIALS, 2024, 480