Visible-Light-Photocatalyzed Metal-Free C-H Heteroarylation of Heteroarenes at Room Temperature: A Sustainable Synthesis of Biheteroaryls

被引：65
|
作者：
Maity, Pintu [1 ]
Kundu, Debasish [1 ]
Ranu, Brindaban C. [1 ]
机构：
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 08期
关键词：
Synthetic methods; Photochemistry; C-H heteroarylation; Cross-coupling; Heterocycles; Radical reactions; CROSS-COUPLING REACTION; ARYL DIAZONIUM SALTS; PHOTOREDOX CATALYSIS; DIRECT ARYLATIONS; DIRECT CONVERSION; BORONIC ACIDS; EOSIN Y; AMINO; ANILINES; TRIFLUOROMETHYLATION;
D O I：
10.1002/ejoc.201500006
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient C-H heteroarylation of heteroarenes is achieved through visible-light photoredox-catalyzed diazotization of heteroarylamines in situ by tBuONO at room temperature. A library of functionalized biheteroaryls is obtained by using this protocol. The reaction avoids the use of transition-metal catalysts, additives, and acidic reaction medium.
引用
收藏
页码：1727 / 1734
页数：8
相关论文
共 50 条
  • [31] Visible light C-H amidation of heteroarenes with benzoyl azides
    Brachet, E.
    Ghosh, T.
    Ghosh, I.
    Koenig, B.
    CHEMICAL SCIENCE, 2015, 6 (02) : 987 - 992
  • [32] Visible-Light-Accelerated C-H Sulfinylation of Heteroarenes
    Meyer, Andreas Uwe
    Wimmer, Alexander
    Koenig, Burkhard
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (01) : 409 - 412
  • [33] N-Hydroxyphthalimide imidate esters as amidyl radical precursors in the visible light photocatalyzed C-H amidation of heteroarenes
    Li, Long-Hai
    Wei, Yin
    Shi, Min
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (09) : 1935 - 1940
  • [34] A Metal-Free Approach for BrOnsted Acid Promoted C-H Alkylation of Heteroarenes with Alkyl Peroxides
    Zeng, Yuehua
    Qian, Bo
    Li, Yajun
    Bao, Hongli
    SYNTHESIS-STUTTGART, 2018, 50 (16): : 3250 - 3256
  • [35] Visible-Light-Enabled Allylic C-H Oxidation: Metal-free Photocatalytic Generation of Enones
    Liu, Chao
    Liu, Hui
    Zheng, Xuan
    Chen, Shanyi
    Lai, Qihong
    Zheng, Changlong
    Huang, Mingqiang
    Cai, Kaicong
    Cai, Zhixiong
    Cai, Shunyou
    ACS CATALYSIS, 2022, 12 (02) : 1375 - 1381
  • [36] A Metal-Free Visible-Light Photoredox Construction and Direct C-H Functionalization of Pyridines: Green Synthesis of Polysubstituted Picolinaldehydes
    Zhang, Qun-Liang
    Yu, Qin-Qin
    Ma, Li
    Lu, Xuelian
    Fan, Qing-Tian
    Duan, Tian-Shun
    Zhou, Yirong
    Zhang, Fang-Lin
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 17244 - 17248
  • [37] Metal-free oxidation of sulfides by carbon nitride with visible light illumination at room temperature
    Zhang, Pengfei
    Wang, Yong
    Li, Haoran
    Antonietti, Markus
    GREEN CHEMISTRY, 2012, 14 (07) : 1904 - 1908
  • [38] Metal-Free Oxidative C-H Bond Amination at Ambient Temperature
    Samanta, Rajarshi
    Antonchick, Andrey P.
    SYNLETT, 2012, (06) : 809 - 813
  • [39] Ortho C-H arylation of arenes at room temperature using visible light ruthenium C-H activation
    Sagadevan, Arunachalam
    Charitou, Anastasios
    Wang, Fen
    Ivanova, Maria
    Vuagnat, Martin
    Greaney, Michael F.
    CHEMICAL SCIENCE, 2020, 11 (17) : 4439 - 4443
  • [40] Direct C-H aminocarbonylation of N-heteroarenes with isocyanides under transition metal-free conditions
    Zhou, Zhong
    Ji, Huihui
    Li, Qing
    Zhang, Qian
    Li, Dong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (13) : 2917 - 2922
12345