Recent Advances in Transition-Metal Catalyzed C-H Bond Fluorination

被引:19
|
作者
He, Jiangqi [1 ]
Lou, Shaojie [1 ]
Xu, Danqian [1 ]
机构
[1] Zhejiang Univ Technol, Catalyt Hydrogenat Res Ctr, Zhejiang Key Lab Green Pesticides & Cleaner Prod, Hangzhou 310014, Zhejiang, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
transition-metal catalysis; fluorination; C-H bond activation; selective; directing groups; COPPER-MEDIATED FLUORINATION; FORMING REDUCTIVE ELIMINATION; LATE-STAGE; ELECTROPHILIC FLUORINATION; PD-IV; ACIDS; TRIFLUOROMETHYLATION; MECHANISM; MILD; MONO;
D O I
10.6023/cjoc201512040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Organofluorine compounds are widely found in pharmaceuticals, agrochemicals, and materials due to their special properties. However, development of transformations to incorporate fluorine atom is usually a great challenge, because of its highly electronegative nature. Transition-metal catalyzed C-H bond fluorination has significant advantages in atom-economy, reaction diversity and environmental friendliness in comparison with the traditional transition-metal catalyzed cross-coupling approaches since it obviates the use of pre-functionalized substrates. In the past decade, C-H bond fluorination strategy has emerged as a powerful protocol to access new C-F bonds. This review presents the state of art for transition-metal catalyzed C-H bond fluorination. The existing problems and limitations of the field are summarized and the outlook of the area is also prospected.
引用
收藏
页码:1218 / 1228
页数:11
相关论文
共 70 条
  • [1] [Anonymous], 2012, ACC CHEM RES, P777
  • [2] Synthesis and Reactivity of a Mono-σ-Aryl Palladium(IV) Fluoride Complex
    Ball, Nicholas D.
    Sanford, Melanie S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) : 3796 - +
  • [3] Organic fluorine compounds: a great opportunity for enhanced materials properties
    Berger, Ricarda
    Resnati, Giuseppe
    Metrangolo, Pierangelo
    Weber, Edwin
    Hulliger, Juerg
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) : 3496 - 3508
  • [4] Iron(II)-Catalyzed Benzylic Fluorination
    Bloom, Steven
    Pitts, Cody Ross
    Woltornist, Ryan
    Griswold, Andrew
    Holl, Maxwell Gargiulo
    Lectka, Thomas
    [J]. ORGANIC LETTERS, 2013, 15 (07) : 1722 - 1724
  • [5] A Polycomponent Metal-Catalyzed Aliphatic, Allylic, and Benzylic Fluorination
    Bloom, Steven
    Pitts, Cody Ross
    Miller, David Curtin
    Haselton, Nathan
    Holl, Maxwell Gargiulo
    Urheim, Ellen
    Lectka, Thomas
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (42) : 10580 - 10583
  • [6] Palladium-Catalyzed Allylic C-H Fluorination
    Braun, Marie-Gabrielle
    Doyle, Abigail G.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) : 12990 - 12993
  • [7] Late-stage [18F]fluorination: new solutions to old problems
    Brooks, Allen F.
    Topczewski, Joseph J.
    Ichiishi, Naoko
    Sanford, Melanie S.
    Scott, Peter J. H.
    [J]. CHEMICAL SCIENCE, 2014, 5 (12) : 4545 - 4553
  • [8] Camasso NM, 2014, J AM CHEM SOC, V136, P12771, DOI [10.1021/Ja507056u, 10.1021/ja507056u]
  • [9] Palladium(II)-Catalyzed Selective Monofluorination of Benzoic Acids Using a Practical Auxiliary: A Weak-Coordination Approach
    Chan, Kelvin S. L.
    Wasa, Masayuki
    Wang, Xisheng
    Yu, Jin-Quan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) : 9081 - 9084
  • [10] Palladium-Catalyzed ortho-Selective C-H Fluorination of Oxalyl Amide-Protected Benzylamines
    Chen, Changpeng
    Wang, Chao
    Zhang, Jingyu
    Zhao, Yingsheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (02): : 942 - 949