Rh-Catalyzed gem-Difluoroallylation of N-Tosylhydrazones

被引：1
|
作者：
Wang Jiazhuang [1 ]
Teng Liguo [1 ]
Xiong Shaoqi [1 ]
Xiao Tiebo [1 ]
Jiang Yubo [1 ]
机构：
[1] Kunming Univ Sci & Technol, Fac Sci, Kunming 650500, Yunnan, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 42卷 / 11期
基金：
中国国家自然科学基金;
关键词：
N-tosylhydrazones; 3,3-difluoroallyl sulfides; Rh-catalysis; gem-difluoroallylation; CROSS-COUPLING REACTIONS; ALPHA-DIAZO ESTERS; TERMINAL ALKYNES; MEDIATED TRIFLUOROMETHYLATION; VERSATILE REAGENTS; DIRECT ALKYLATION; TMSCF3; DIFLUOROOLEFINATION; DIAZOESTERS; FLUORINE;
D O I：
10.6023/cjoc202205054
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rhodium-catalyzed rearrangement reaction of N-tosylhydrazones and 3,3-difluoroallyl sulfides was developed. This protocal provided a facile and efficient synthesis route to gem-difluoroallyl compounds with medium to excellent yield and good functional group tolerance. Moreover, the applicability of current method has been demonstrated by one-pot reaction, gram-scale synthesis and further transformations.
引用
收藏
页码：3658 / 3667
页数：10
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  • [1] Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes
    Alonso, Concepcion
    Martinez de Marigorta, Eduardo
    Rubiales, Gloria
    Palacios, Francisco
    [J]. CHEMICAL REVIEWS, 2015, 115 (04) : 1847 - 1935
  • [2] Synthesis and characterization of a novel difluoromethylene phosphonic acid functionalized polymer
    Alter, Christian
    Hoge, Berthold
    [J]. JOURNAL OF APPLIED POLYMER SCIENCE, 2018, 135 (42)
  • [3] N-tosylhydrazones as reagents for cross-coupling reactions:: A route to polysubstituted olefins
    Barluenga, José
    Moriel, Patricia
    Valdes, Carlos
    Aznar, Fernando
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) : 5587 - 5590
  • [4] Arylation of α-Chiral Ketones by Palladium-Catalyzed Cross-Coupling Reactions of Tosylhydrazones with Aryl Halides
    Barluenga, Jose
    Escribano, Maria
    Aznar, Fernando
    Valdes, Carlos
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (38) : 6856 - 6859
  • [5] Straightforward Synthesis of Ethers: Metal-Free Reductive Coupling of Tosylhydrazones with Alcohols or Phenols
    Barluenga, Jose
    Tomas-Gamasa, Maria
    Aznar, Fernando
    Valdes, Carlos
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (29) : 4993 - 4996
  • [6] Difluoromethylene at the γ-Lactam α-Position Improves 11-Deoxy-8-aza-PGE1 Series EP4 Receptor Binding and Activity: 11-Deoxy-10,10-difluoro-8-aza-PGE1 Analog (KMN-159) as a Potent EP4 Agonist
    Barrett, Stephen D.
    Holt, Melissa C.
    Kramer, James B.
    Germain, Bradlee
    Ho, Chi S.
    Ciske, Fred L.
    Kornilov, Andrei
    Colombo, Joseph M.
    Uzieblo, Adam
    O'Malley, James P.
    Owen, Thomas A.
    Stein, Adam J.
    Morano, Maria I.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (09) : 4731 - 4741
  • [7] Maraviroc
    Carter, Natalie J.
    Keating, Gillian M.
    [J]. DRUGS, 2007, 67 (15) : 2277 - 2288
  • [8] Carbon-Carbon Bond Formation: Palladium-Catalyzed Oxidative Cross-Coupling of N-Tosylhydrazones with Allylic Alcohols
    Chen, Huoji
    Huang, Li
    Fu, Wei
    Liu, Xiaohang
    Jiang, Huanfeng
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (34) : 10497 - 10500
  • [9] Palladium-Catalyzed Coupling of Propargylic Carbonates with N-Tosylhydrazones: Highly Selective Synthesis of Substituted Propargylic N-Sulfonylhydrazones and Vinylallenes
    Chen, Zi-Sheng
    Duan, Xin-Hua
    Wu, Lu-Yong
    Ali, Shaukat
    Ji, Ke-Gong
    Zhou, Ping-Xin
    Liu, Xue-Yuan
    Liang, Yong-Min
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) : 6918 - 6921
  • [10] Synthesis of thioethers via metal-free reductive coupling of tosylhydrazones with thiols
    Ding, Qiuping
    Cao, Banpeng
    Yuan, Jianjun
    Liu, Xianjin
    Peng, Yiyuan
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (03) : 748 - 751
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