Copper-Catalyzed Multicomponent Trifluoromethylphosphorothiolation of Alkenes: Access to CF3-Containing Alkyl Phosphorothioates

被引:29
作者
Zhang, Pengbo [1 ]
Yu, Guo [1 ]
Li, Wenwu [1 ]
Shu, Zhigang [1 ]
Wang, Longyu [1 ]
Li, Zhaoting [1 ]
Gao, Xia [1 ]
机构
[1] Xinxiang Med Univ, Sch Publ Hlth, Xinxiang 453003, Henan, Peoples R China
关键词
P(O)H COMPOUNDS; THIOLS; PHOSPHINOTHIOATES; PHOSPHONATES; REAGENTS; ACIDS;
D O I
10.1021/acs.orglett.1c01985
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented copper-catalyzed multicomponent radical-based reaction involving alkenes, P(O)H compounds, sulfur powder, and Togni reagent II at room temperature has been developed. A variety of highly functionalized CF3-containing S-alkyl phosphorothioates can be directly prepared from a wide range of activated and unactivated alkenes. Moreover, this protocol highlights its potential in the late-stage functionalization of complex molecules and opens up a new avenue for the construction of C(sp(3))-S-P bonds.
引用
收藏
页码:5848 / 5852
页数:5
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共 35 条
  • [1] Visible-Light-Mediated Trifluoromethylation/Benzylation of Styrenes Catalyzed by 4-CzIPN
    Bao, Qiao-Fei
    Xia, Yu
    Li, Ming
    Wang, Yu-Zhao
    Liang, Yong-Min
    [J]. ORGANIC LETTERS, 2020, 22 (19) : 7757 - 7761
  • [2] Multicomponent reactions: advanced tools for sustainable organic synthesis
    Cioc, Razvan C.
    Ruijter, Eelco
    Orru, Romano V. A.
    [J]. GREEN CHEMISTRY, 2014, 16 (06) : 2958 - 2975
  • [3] Recent developments in nickel-catalyzed intermolecular dicarbofunctionalization of alkenes
    Derosa, Joseph
    Apolinar, Omar
    Kang, Taeho
    Tran, Van T.
    Engle, Keary M.
    [J]. CHEMICAL SCIENCE, 2020, 11 (17) : 4287 - 4296
  • [4] Z-Selective ring opening of vinyl oxetanes with dialkyl dithiophosphate nucleophiles
    Guo, B.
    Njardarson, J. T.
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (92) : 10802 - 10804
  • [5] Mild stereoselective formation of tri- and tetrasubstituted olefins by regioselective ring opening of 1,1-disubstituted vinyl oxiranes with dialkyl dithiophosphates
    Guo, Boying
    Vitaku, Edon
    Njardarson, Jon T.
    [J]. TETRAHEDRON LETTERS, 2014, 55 (21) : 3232 - 3234
  • [6] Modern Synthetic Approaches to Phosphorus-Sulfur Bond Formation in Organophosphorus Compounds
    Jones, David J.
    O'Leary, Eileen M.
    O'Sullivan, Timothy P.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (14) : 2801 - 2846
  • [7] A Robust Methodology for the Synthesis of Phosphorothioates, Phosphinothioates and Phosphonothioates
    Jones, David J.
    O'Leary, Eileen M.
    O'Sullivan, Timothy P.
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (09) : 1825 - 1830
  • [8] Synthesis and application of phosphonothioates, phosphonodithioates, phosphorothioates, phosphinothioates and related compounds
    Jones, David J.
    O'Leary, Eileen M.
    O'Sullivan, Timothy P.
    [J]. TETRAHEDRON LETTERS, 2018, 59 (49) : 4279 - 4292
  • [9] Synthesis of symmetrically and unsymmetrically substituted S,S-dialkyl phosphonodithioates
    Jones, David J.
    O'Leary, Eileen M.
    O'Sullivan, Timothy P.
    [J]. TETRAHEDRON LETTERS, 2017, 58 (44) : 4212 - 4214
  • [10] Synthesis of novel phosphorothioates and phosphorodithioates and their differential inhibition of cholinesterases
    Kaboudin, Babak
    Emadi, Saeed
    Hadizadeh, Atefeh
    [J]. BIOORGANIC CHEMISTRY, 2009, 37 (04) : 101 - 105