Visible-Light-Mediated C-I Difluoroallylation with an α-Aminoalkyl Radical as a Mediator

被引:45
作者
Yue, Fuyang [1 ]
Dong, Jianyang [1 ]
Liu, Yuxiu [1 ]
Wang, Qingmin [1 ]
机构
[1] Nankai Univ, Coll Chem, Frontiers Sci Ctr New Organ Matter, State Key Lab Elementoorgan Chem,Res Inst Element, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
HALOGEN-ATOM-TRANSFER; BIOLOGICAL-ACTIVITY; UNACTIVATED ALKYL; TRIFLUOROMETHYLATION; DERIVATIVES; GENERATION; CATALYSIS; DESIGN; AGENTS;
D O I
10.1021/acs.orglett.1c02905
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report a protocol for direct visible-light-mediated C-I difluoroallylation reactions of a-trifluoromethyl arylalkenes with alkyl iodides at room temperature with an alpha-aminoalkyl radical as a mediator. The protocol permits efficient functionalization of various alpha-trifluoromethyl arylalkenes with cyclic and acyclic primary, secondary, and tertiary alkyl iodides and is scalable to the gram level. This mild protocol uses an inexpensive mediator and is suitable for late-stage functionalization of complex natural products and drugs.
引用
收藏
页码:7306 / 7310
页数:5
相关论文
共 36 条
  • [11] RATES OF HALOGEN ATOM TRANSFER TO MANGANESE CARBONYL RADICALS
    HERRICK, RS
    HERRINTON, TR
    WALKER, HW
    BROWN, TL
    [J]. ORGANOMETALLICS, 1985, 4 (01) : 42 - 45
  • [12] Visible-Light-Induced Photocatalytic Reductive Transformations of Organohalides
    Kim, Hyejin
    Lee, Chulbom
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (49) : 12303 - 12306
  • [13] 3-Aminoperylene and ascorbate in aqueous SDS, one green laser flash ... and action! Sustainably detoxifying a recalcitrant chloro-organic
    Kohlmann, Tim
    Naumann, Robert
    Kerzig, Christoph
    Goez, Martin
    [J]. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2017, 16 (11) : 1613 - 1622
  • [14] Catalysis of Radical Cyclizations from Alkyl Iodides under H2: Evidence for Electron Transfer from [CpV(CO)3H]-
    Kuo, Jonathan L.
    Lorenc, Chris
    Abuyuan, Janine M.
    Norton, Jack R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (13) : 4512 - 4516
  • [15] Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Allylic Defluorinative Reductive Cross-Coupling
    Lan, Yun
    Yang, Feiyan
    Wang, Chuan
    [J]. ACS CATALYSIS, 2018, 8 (10): : 9245 - 9251
  • [16] Photoredox Generation of Carbon-Centered Radicals Enables the Construction of 1,1-Difluoroalkene Carbonyl Mimics
    Lang, Simon B.
    Wiles, Rebecca J.
    Kelly, Christopher B.
    Molander, Gary A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (47) : 15073 - 15077
  • [17] A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes
    Le, Chip
    Chen, Tiffany Q.
    Liang, Tao
    Zhang, Patricia
    MacMillan, David W. C.
    [J]. SCIENCE, 2018, 360 (6392) : 1010 - +
  • [18] Fluorinated Proteins: From Design and Synthesis to Structure and Stability
    Marsh, E. Neil G.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (10) : 2878 - 2886
  • [19] UVA- and Visible-Light-Mediated Generation of Carbon Radicals from Organochlorides Using Nonmetal Photocatalyst
    Matsubara, Ryosuke
    Yabuta, Tatsushi
    Idros, Ubaidah Md
    Hayashi, Masahiko
    Ema, Fumitoshi
    Kobori, Yasuhiro
    Sakata, Ken
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (16) : 9381 - 9390
  • [20] Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development
    Matsui, Jennifer K.
    Lang, Simon B.
    Heitz, Drew R.
    Molander, Gary A.
    [J]. ACS CATALYSIS, 2017, 7 (04): : 2563 - 2575