Silver-Catalyzed Late-Stage Fluorination

被引:277
作者
Tang, Pingping [1 ]
Furuya, Takeru [1 ]
Ritter, Tobias [1 ]
机构
[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
关键词
REDUCTIVE ELIMINATION; FUNCTIONALIZED ARYL; BOND FORMATION; REACTIVITY; CHEMISTRY;
D O I
10.1021/ja105834t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carbon-fluorine bond formation by transition metal catalysis is difficult, and only a few methods for the synthesis of aryl fluorides have been developed. All reported transition-metal-catalyzed fluorination reactions for the synthesis of functionalized arenes are based on palladium. Here we present silver catalysis for carbon-fluorine bond formation. Our report is the first example of the use of the transition metal silver to form carbon-heteroatom bonds by cross-coupling catalysis. The functional group tolerance and substrate scope presented here have not been demonstrated for any other fluorination reaction to date.
引用
收藏
页码:12150 / 12154
页数:5
相关论文
共 47 条
  • [1] Nucleophilic routes to selectively fluorinated aromatics
    Adams, DJ
    Clark, JH
    [J]. CHEMICAL SOCIETY REVIEWS, 1999, 28 (04) : 225 - 231
  • [2] Reversible C-F bond formation and the Au-catalyzed hydrofluorination of alkynes
    Akana, Jennifer A.
    Bhattacharyya, Koyel X.
    Mueller, Peter
    Sadighi, Joseph P.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (25) : 7736 - +
  • [3] Silver-mediated synthesis of heterocycles
    Alvarez-Corral, Miriam
    Munoz-Dorado, Manuel
    Rodirguez-Garcia, Ignacio
    [J]. CHEMICAL REVIEWS, 2008, 108 (08) : 3174 - 3198
  • [4] Efficient Synthesis of Aryl Fluorides
    Anbarasan, Pazhamalai
    Neumann, Helfried
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (12) : 2219 - 2222
  • [5] Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom
    Babudri, Francesco
    Farinola, Gianluca M.
    Naso, Francesco
    Ragni, Roberta
    [J]. CHEMICAL COMMUNICATIONS, 2007, (10) : 1003 - 1022
  • [6] 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 - +
  • [7] On aromatic fluoric compounds, I A new method for its representation
    Balz, G
    Schiemann, G
    [J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1927, 60 : 1186 - 1190
  • [8] Baudoux J., 2007, Org. React, V69, P347, DOI DOI 10.1002/0471264180.OR069.02
  • [9] Davis A. G., 2008, TIN CHEM FUNDAMENTAL
  • [10] de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V1