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
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
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共 65 条
  • [1] Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage
    Ackermann, Lutz
    Vicente, Ruben
    Kapdi, Anant R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) : 9792 - 9826
  • [2] STEREOCONTROLLED FORMATION OF FUNCTIONALIZED ERYTHRO-1,2-DIOLS VIA HYDROBORATION OF 2-ALKYL-4,5-DIHYDROFURANS
    AMOUROUX, R
    SLASSI, A
    SALUZZO, C
    [J]. HETEROCYCLES, 1993, 36 (09) : 1965 - 1969
  • [3] [Anonymous], 2020, ANGEW CHEM-GER EDIT, V132, P465
  • [4] [Anonymous], 2014, ANGEW CHEM-GER EDIT, V127, P1505
  • [5] [Anonymous], 2009, ANGEW CHEM, V121, P9976
  • [6] [Anonymous], 2019, ANGEW CHEM-GER EDIT, V131, P12414
  • [7] [Anonymous], 2011, ANGEW CHEM, V123, P7618
  • [8] [Anonymous], 2018, ANGEW CHEM, V130, P10188
  • [9] Arceo E, 2013, NAT CHEM, V5, P750, DOI [10.1038/NCHEM.1727, 10.1038/nchem.1727]
  • [10] Synthesis of 6-(4,5-dihydrofuran-2-yl)- and 6-(tetrahydrofuran-2-yl)purine bases and nucleosides
    Bambuch, Vitezslav
    Pohl, Radek
    Hocek, Michal
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (16) : 2783 - 2788