Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines

被引：178
作者：
Egami, Hiromichi [1 ,2 ]
Kawamura, Shintaro [1 ,2 ]
Miyazaki, Ayako [1 ,2 ]
Sodeoka, Mikiko [1 ,2 ,3 ]
机构：
[1] RIKEN, Synthet Organ Chem Lab, Wako, Saitama 3510198, Japan
[2] Japan Sci & Technol Agcy, Sodeoka Live Cell Chem Project, ERATO, Wako, Saitama 3510198, Japan
[3] RIKEN Ctr Sustainable Resource Sci, Wako, Saitama 3510198, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 30期
关键词：
amines; aziridines; copper; multicomponent reactions; trifluoromethylation; COPPER-CATALYZED TRIFLUOROMETHYLATION; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION; TERMINAL ALKENES; FLUORINE; EFFICIENT; OXYTRIFLUOROMETHYLATION; HYDROTRIFLUOROMETHYLATION; ALLYLSILANES; REAGENTS;
D O I：
10.1002/anie.201303350
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A multitalented system: N-Migratory oxytrifluoromethylation and one-pot three-component reactions of allylamines as well as the aminotrifluoromethylation of alkenyl amines all proceeded efficiently in the presence of the Togni reagent (1) and CuI to afford a variety of β-trifluoromethylamine derivatives (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：7841 / 7844
页数：4
相关论文
共 83 条
  • [1] The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes
    Allen, Anna E.
    MacMillan, David W. C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) : 4986 - +
  • [2] Recent Progress in Catalytic Aromatic Trifluoromethylation
    Amii, Hideki
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2011, 69 (07) : 752 - 762
  • [3] [Anonymous], 2005, ANGEW CHEM
  • [4] [Anonymous], 2009, Angew. Chem., Int. Ed.
  • [5] [Anonymous], 2006, ANGEW CHEM, V118, P4305
  • [6] [Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1135/CCCC2011078
  • [7] Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine
  • [8] Using Fluorine Nuclear Magnetic Resonance To Probe the Interaction of Membrane-Active Peptides with the Lipid Bilayer
    Buer, Benjamin C.
    Chugh, Jeetender
    Al-Hashimi, Hashim M.
    Marsh, E. Neil G.
    [J]. BIOCHEMISTRY, 2010, 49 (27) : 5760 - 5765
  • [9] Helix propensity of highly fluorinated amino acids
    Chiu, Hsien-Po
    Suzuki, Yuta
    Gullickson, Donald
    Ahmad, Raheel
    Kokona, Bashkim
    Fairman, Robert
    Cheng, Richard P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) : 15556 - 15557
  • [10] Effect of Highly Fluorinated Amino Acids on Protein Stability at a Solvent-Exposed Position on an Internal Strand of Protein G B1 Domain
    Chiu, Hsien-Po
    Kokona, Bashkim
    Fairman, Robert
    Cheng, Richard P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (37) : 13192 - 13193
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