Generation of CF3-Containing Epoxides and Aziridines by Visible-Light-Driven Trifluoromethylation of Allylic Alcohols and Amines

被引:177
作者
Kim, Eunjin [1 ]
Choi, Sungkyu [1 ]
Kim, Heejeong [1 ]
Cho, Eun Jin [1 ]
机构
[1] Hanyang Univ, Dept Chem & Appl Chem, Ansan 426791, Kyeonggido, South Korea
基金
新加坡国家研究基金会;
关键词
epoxides; nucleophilic addition; radical reactions; trifluoromethylation; visible light; PALLADIUM-CATALYZED TRIFLUOROMETHYLATION; OXYTRIFLUOROMETHYLATION; PHOTOCATALYSIS; ALKENES; ACIDS; ARYL;
D O I
10.1002/chem.201300564
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Radical reactions! Efficient methods for the generation of CF 3-containing epoxides and aziridines have been developed (see scheme). A variety of allylic alcohols and allylic amines were transformed into the corresponding epoxides and aziridines by using [Ru(bpy)3]Cl 2 (bpy=2,2′-bipyridine), CF3I, and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (or N,N,N′,N′- tetramethylethylenediamine, TMEDA) under visible-light irradiation. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:6209 / 6212
页数:4
相关论文
共 43 条
  • [1] Stereoselective synthesis of CF3-substituted aziridines by Lewis acid-mediated aziridination of aldimines with diazoacetates
    Akiyama, T
    Ogi, S
    Fuchibe, K
    [J]. TETRAHEDRON LETTERS, 2003, 44 (21) : 4011 - 4013
  • [2] [Anonymous], 2009, ANGEW CHEM INT ED, V48, P9785
  • [3] [Anonymous], 2011, ANGEW CHEM INT ED, V50, P7171
  • [4] The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates
    Cho, Eun Jin
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2011, 13 (24) : 6552 - 6555
  • [5] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides
    Cho, Eun Jin
    Senecal, Todd D.
    Kinzel, Tom
    Zhang, Yong
    Watson, Donald A.
    Buchwald, Stephen L.
    [J]. SCIENCE, 2010, 328 (5986) : 1679 - 1681
  • [6] Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization
    Condie, Allison G.
    Gonzalez-Gomez, Jose C.
    Stephenson, Corey R. J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) : 1464 - +
  • [7] REDUCTION OF 5-(TRIFLUOROMETHYL)ISOXAZOLES WITH LITHIUM ALUMINUM-HYDRIDE - SYNTHESIS OF (2,2,2-TRIFLUOROETHYL)AZIRIDINES
    FELIX, CP
    KHATIMI, N
    LAURENT, AJ
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) : 3907 - 3909
  • [8] Functionally Diverse Nucleophilic Trapping of Iminium Intermediates Generated Utilizing Visible Light
    Freeman, David B.
    Furst, Laura
    Condie, Allison G.
    Stephenson, Corey R. J.
    [J]. ORGANIC LETTERS, 2012, 14 (01) : 94 - 97
  • [9] TRANSITION-METAL COMPLEX CATALYZED POLYFLUOROALKYLATION - A FACILE SYNTHESIS OF FLUORINE-CONTAINING OXIRANES AND ENYNES
    FUCHIKAMI, T
    SHIBATA, Y
    URATA, H
    [J]. CHEMISTRY LETTERS, 1987, (03) : 521 - 524
  • [10] Catalysis for fluorination and trifluoromethylation
    Furuya, Takeru
    Kamlet, Adam S.
    Ritter, Tobias
    [J]. NATURE, 2011, 473 (7348) : 470 - 477