Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

被引:526
作者
Ma, Jun-An
Cahard, Dominique
机构
[1] Univ Rouen, INSA Rouen, UMR 6014 CNRS LIRCOF, F-76821 Mont St Aignan, France
[2] Tianjin Univ, Dept Chem, Tianjin 300072, Peoples R China
关键词
trifluoromethylation; fluorinated compounds; nucleophilic reagents; electrophilic reagents; radical reactions;
D O I
10.1016/j.jfluchem.2007.04.026
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Recent advances in the development of new strategies in nucleophilic, electrophilic, and radical trifluoromethylations are reviewed. The emphasis is given to the description of the trifluoromethylating agents, their activation mode, their reaction with carbonyl compounds and derivatives, as well as application in asymmetric synthesis. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:975 / 996
页数:22
相关论文
共 161 条
  • [1] Adachi K., 2003, Japanese Patent, Patent No. 20030388769
  • [2] Nucleophilic trifluoromethylation using trifluoromethyl iodide.: A new and simple alternative for the trifluoromethylation of aldehydes and ketones
    Aït-Mohand, S
    Takechi, N
    Médebielle, M
    Dolbier, WR
    [J]. ORGANIC LETTERS, 2001, 3 (26) : 4271 - 4273
  • [3] UNUSUAL REACTIONS RESULTING FROM THE ADDITION ON OLEFINS OF TRIFLUOROMETHYL RADICALS OBTAINED FROM DISSOCIATIVE ELECTRON-TRANSFER BETWEEN ELECTROCHEMICALLY GENERATED AROMATIC ANION RADICALS AND TRIFLUOROMETHYL BROMIDE
    ANDRIEUX, CP
    GELIS, L
    SAVEANT, JM
    [J]. TETRAHEDRON LETTERS, 1989, 30 (37) : 4961 - 4964
  • [4] Coupling of fluoroform with aldehydes using an electrogenerated base
    Barhdadi, R
    Troupel, M
    Périchon, J
    [J]. CHEMICAL COMMUNICATIONS, 1998, (12) : 1251 - 1252
  • [5] SYNTHESIS AND PROPERTIES OF (TRIFLUOROMETHYL)TRICHLOROSILANE, A VERSATILE PRECURSOR FOR CF3SI COMPOUNDS
    BECKERS, H
    BURGER, H
    BURSCH, P
    RUPPERT, I
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 316 (1-2) : 41 - 50
  • [6] A xanthate transfer radical process for the introduction of the trifluoromethyl group
    Bertrand, F
    Pevere, V
    Quiclet-Sire, B
    Zard, SZ
    [J]. ORGANIC LETTERS, 2001, 3 (07) : 1069 - 1071
  • [7] Synthetic uses of thioesters of trifluoromethylated acids. Part 2. Reactions with alkenes
    Billard, T
    Roques, N
    Langlois, BR
    [J]. TETRAHEDRON LETTERS, 2000, 41 (17) : 3069 - 3072
  • [8] New stable reagents for the nucleophilic trifluoromethylation. Part 2: Trifluoromethylation with silylated hemiaminals of trifluoroacetaldehyde
    Billard, T
    Langlois, BR
    Blond, G
    [J]. TETRAHEDRON LETTERS, 2000, 41 (45) : 8777 - 8780
  • [9] New stable reagents for the nucleophilic trifluoromethylation.: 1.: Trifluoromethylation of carbonyl compounds with N-formylmorpholine derivatives
    Billard, T
    Bruns, S
    Langlois, BR
    [J]. ORGANIC LETTERS, 2000, 2 (14) : 2101 - 2103
  • [10] Billard T, 2001, EUR J ORG CHEM, V2001, P1467