Visible-Light-Mediated Alkylation of Thiophenols via Electron Donor-Acceptor Complexes Formed between Two Reactants

被引:34
作者
Cai, Yi-Ping [1 ]
Nie, Fang-Yuan [1 ]
Song, Qin-Hua [1 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
基金
中国国家自然科学基金;
关键词
C-S; ARYL; EFFICIENT; SULFUR; THIOLS; IODIDES;
D O I
10.1021/acs.joc.1c01433
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A metal-free, photocatalyst-free, photochemical system was developed for the direct alkylation of thiophenols via electron donor-acceptor (EDA) complexes (K-EDA = 145 M-1) between two reactants, N-hydroxyphthalimide esters as acceptors and thiophenol anions as donors, in the presence of a tertiary amine. The EDA complexes in the reaction system have a broad range of visible-light absorption (400-650 nm) and can trigger the reaction effectively under sunlight.
引用
收藏
页码:12419 / 12426
页数:8
相关论文
共 49 条
  • [1] REMOTE PARTICIPATION DURING PHOTOOXIDATION AT SULFUR - EVIDENCE FOR SULFURANE INTERMEDIATES
    CLENNAN, EL
    YANG, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (16) : 4477 - 4487
  • [2] Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters
    Cornella, Josep
    Edwards, Jacob T.
    Qin, Tian
    Kawamura, Shuhei
    Wang, Jie
    Pan, Chung-Mao
    Gianatassio, Ryan
    Schmidt, Michael
    Eastgate, Martin D.
    Baran, Phil S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (07) : 2174 - 2177
  • [3] Regio- and Enantioselective Intermolecular Hydroacylation: Substrate-Directed Addition of Salicylaldehydes to Homoallylic Sulfides
    Coulter, Matthew M.
    Kou, Kevin G. M.
    Galligan, Baye
    Dong, Vy M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (46) : 16330 - 16333
  • [4] 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
  • [5] Davies J., 2015, ANGEW CHEM INT EDIT, V54, P14017, DOI DOI 10.1002/anie.201507641
  • [6] Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation
    Delcaillau, Tristan
    Bismuto, Alessandro
    Lian, Zhong
    Morandi, Bill
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (05) : 2110 - 2114
  • [7] Syntheses of Sulfides and Selenides through Direct Oxidative Functionalization of C(sp3)-H Bond
    Du, Bingnan
    Jin, Bo
    Sun, Peipei
    [J]. ORGANIC LETTERS, 2014, 16 (11) : 3032 - 3035
  • [8] Photoinduced decarboxylative borylation of carboxylic acids
    Fawcett, Alexander
    Pradeilles, Johan
    Wang, Yahui
    Mutsuga, Tatsuya
    Myers, Eddie L.
    Aggarwal, Varinder K.
    [J]. SCIENCE, 2017, 357 (6348) : 283 - 286
  • [9] Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry
    Feng, Minghao
    Tang, Bingqing
    Liang, Steven H.
    Jiang, Xuefeng
    [J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (11) : 1200 - 1216
  • [10] Highly efficient and functional-group-tolerant catalysts for the palladium-catalyzed coupling of aryl chlorides with thiols
    Fernandez-Rodriguez, Manuel A.
    Shen, Qilong
    Hartwig, John F.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (30) : 7782 - 7796