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

被引:125
|
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
  • [31] Catalyst-free visible light-induced decarboxylative amination of glycine derivatives with azo compounds
    Zhou, Cen
    Huang, Xiaozhou
    Hu, Yaqing
    Wu, Junyan
    Zheng, Ying
    Zhang, Xiao
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (02) : 465 - 469
  • [32] Green synthesis of 1,3-oxazines by visible light-promoted catalyst-free C-H activation/cyclization of tertiary amines
    Saikia, B. Shriya
    Deb, Mohit L.
    Baruah, Pranjal K.
    ENVIRONMENTAL CHEMISTRY LETTERS, 2022, 20 (01) : 109 - 118
  • [33] Controlled Relay Process to Access N-Centered Radicals for Catalyst-free Amidation of Aldehydes under Visible Light
    Lee, Wongyu
    Jeon, Hyun Ji
    Jung, Hoimin
    Kim, Dongwook
    Seo, Sangwon
    Chang, Sukbok
    CHEM, 2021, 7 (02): : 495 - 508
  • [34] Visible-Light Induced C(sp3)-H Functionalization for the Formation of C-N Bonds under Metal Catalyst-Free Conditions
    Chen, Jin-Yang
    Wu, Wenfeng
    Li, Qiang
    Wei, Wen-Ting
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (14) : 2770 - 2777
  • [35] Hybrid organometallo-silica catalysts for sustainable visible-light promoted olefin isomerization
    Martinez-Aguirre, Monica
    Serrano, Elena
    Ezquerro, Cintia
    Lalinde, Elena
    Berenguer, Jesus R.
    Garcia-Martinez, Javier
    Rodriguez, Miguel A.
    CATALYSIS TODAY, 2023, 422
  • [36] Visible-light promoted one-pot synthesis of pyrazoles from alkynes and hydrazines
    Meng, Yunge
    Zhang, Te
    Gong, Xinchi
    Zhang, Min
    Zhu, Chunyin
    TETRAHEDRON LETTERS, 2019, 60 (02) : 171 - 174
  • [37] Catalyst-Free and Solvent-Free Visible Light Assisted Synthesis of Tetrahydrobenzo[b]Pyran Scaffolds at Room Temperature
    Mohamadpour, Farzaneh
    POLYCYCLIC AROMATIC COMPOUNDS, 2022, 42 (10) : 7607 - 7615
  • [38] Visible-light-induced radical cascade cyclization: a catalyst-free synthetic approach to trifluoromethylated heterocycles
    Yang, Chuan
    Shi, Wei
    Tian, Jian
    Guo, Lin
    Zhao, Yating
    Xia, Wujiong
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 118 - 124
  • [39] Recent Developments on Catalyst-Free, Visible-Light-Triggered Synthesis of Heterocyclic Scaffolds and Their Mechanistic Study
    Goswami, Munmee
    Dutta, Arup
    Paul, Pooja
    Nongkhlaw, Rishanlang
    CHEMISTRYSELECT, 2021, 6 (36): : 9684 - 9700
  • [40] Visible-light promoted α-alkylation of glycine derivatives with alkyl boronic acids
    Wang, Jiayuan
    Su, Yingpeng
    Quan, Zhengjun
    Li, Jun
    Yang, Jie
    Yuan, Yong
    Huo, Congde
    CHEMICAL COMMUNICATIONS, 2021, 57 (15) : 1959 - 1962