Catalyst-Free Intermolecular Sulfonyl/Fluoromethyl Heteroarylation of Vinyl Ethers via Visible-Light-Induced Charge Transfer

被引：6
作者：
Long, Tianyu [1 ]
Pan, Shiwei [1 ]
Zhu, Shengqing [1 ]
Chu, Lingling [1 ]
机构：
[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Ctr Adv Low Dimens Mat, State Key Lab Modificat Chem Fibers & Polymer Mat, Shanghai 201620, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2022年 / 28卷 / 15期
基金：
中国国家自然科学基金;
关键词：
alkenes; catalyst-free reactions; difunctionalization; electron-donor-acceptor complex; radical cascade; DONOR-ACCEPTOR COMPLEX; ARYLATION; ALKYLATION; FLUORINE; ROUTES; DRIVEN;
D O I：
10.1002/chem.202104080
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report a visible-light-induced three-component sulfonyl-heteroarylation of vinyl ethers with sulfinates and five-membered heteroaryl chlorides. This protocol proceeds via electron-donor-acceptor (EDA) complexes between sulfinates and heteroaryl chlorides, giving beta-sulfonyl alkyl five-membered heteroarenes with high efficiency and excellent regioselectivity under mild and catalyst-free conditions. Utilization of CF3SO2Na or CF2HSO2Na as coupling partners further achieves three-component fluoromethyl-arylation of vinyl ethers, furnishing a series of valuable CF3/CF2H-incorporated alkyl heterocycles under mild conditions.
引用
收藏
页数：6
相关论文
共 65 条
  • [11] An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals
    Baumann, Marcus
    Baxendale, Ian R.
    Ley, Steven V.
    Nikbin, Nikzad
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 442 - 495
  • [12] 3-Acetoxyquinuclidine as Catalyst in Electron Donor-Acceptor Complex-Mediated Reactions Triggered by Visible Light
    Bosque, Irene
    Bach, Thorsten
    [J]. ACS CATALYSIS, 2019, 9 (10): : 9103 - 9109
  • [13] Palladium-Catalyzed Selective Dehydrogenative Cross-Couplings of Heteroarenes
    Bugaut, Xavier
    Glorius, Frank
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) : 7479 - 7481
  • [14] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles
    Campos, Kevin R.
    [J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1069 - 1084
  • [15] Metal-free, intermolecular carbopyridylation of alkenes via visible-light-induced reductive radical coupling
    Chen, Dan
    Xu, Lei
    Long, Tianyu
    Zhu, Shengqing
    Yang, Jun
    Chu, Lingling
    [J]. CHEMICAL SCIENCE, 2018, 9 (48) : 9012 - 9017
  • [16] Intermolecular, redox-neutral azidoarylation of alkenes via photoredox catalysis
    Chen, Jian
    Zhu, Shengqing
    Qin, Jian
    Chu, Lingling
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (16) : 2336 - 2339
  • [17] Metalated heterocycles and their applications in synthetic organic chemistry
    Chinchilla, R
    Nájera, C
    Yus, M
    [J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2667 - 2722
  • [18] Corey T.P.Y., 2018, VISIBLE LIGHT PHOTOC
  • [19] Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex
    Correia, Jose Tiago M.
    da Silva, Gustavo Piva
    Kisukuri, Camila M.
    Andre, Elias
    Pires, Bruno
    Carneiro, Pablo S.
    Paixao, Marcio W.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (15) : 9820 - 9834
  • [20] Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes
    Crisenza, Giacomo E. M.
    Mazzarella, Daniele
    Melchiorre, Paolo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (12) : 5461 - 5476
1234567