Addition of CF3 across unsaturated moieties: a powerful functionalization tool

被引:715
作者
Merino, Estibaliz [1 ]
Nevado, Cristina [1 ]
机构
[1] Univ Zurich, Dept Chem, CH-8006 Zurich, Switzerland
基金
欧洲研究理事会;
关键词
COPPER-CATALYZED TRIFLUOROMETHYLATION; CARBON MULTIPLE BONDS; RADICAL TRIFLUOROMETHYLATION; ROOM-TEMPERATURE; 3-COMPONENT OXYTRIFLUOROMETHYLATION; PHOTOREDOX CATALYSIS; UNACTIVATED OLEFINS; PRACTICAL SYNTHESIS; ACTIVATED ALKENES; HYDROTRIFLUOROMETHYLATION;
D O I
10.1039/c4cs00025k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In the last few years, the efficient introduction of trifluoromethyl groups in organic molecules has become a major research focus. This review highlights the recent developments enabling the incorporation of CF3 groups across unsaturated moieties, preferentially alkenes, and the mechanistic scenarios governing these transformations. We have specially focused on methods involving the simultaneous formation of C-CF3 and C-C or C-heteroatom bonds by formal addition reactions across p-systems, as such difunctionalization processes hold valuable synthetic potential.
引用
收藏
页码:6598 / 6608
页数:11
相关论文
共 70 条
  • [1] 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
  • [2] Chen P., 2013, SYNTHESIS-STUTTGART, P2919
  • [3] Chen Q.-Y., 1988, J CHEM SOC PERK T, V1, P563
  • [4] Dan-oh Y., 1995, B CHEM SOC JPN, V68, P2993
  • [5] Oxidative Trifluoromethylation of Unactivated Olefins: An Efficient and Practical Synthesis of α-Trifluoromethyl-Substituted Ketones
    Deb, Arghya
    Manna, Srimanta
    Modak, Atanu
    Patra, Tuhin
    Maity, Soham
    Maiti, Debabrata
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) : 9747 - 9750
  • [6] Copper-Catalyzed Trifluoromethylation and Cyclization of Aromatic-Sulfonyl-Group-Tethered Alkenes for the Construction of 1,2-Benzothiazinane Dioxide Type Compounds
    Dong, Xiang
    Sang, Rui
    Wang, Qiang
    Tang, Xiang-Ying
    Shi, Min
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (50) : 16910 - 16915
  • [7] Concise synthesis of oxindole derivatives bearing a 3-trifluoroethyl group: Copper-catalyzed trifluoromethylation of acryloanilides
    Egami, Hiromichi
    Shimizu, Ryo
    Sodeoka, Mikiko
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2013, 152 : 51 - 55
  • [8] Iron-catalyzed trifluoromethylation with concomitant C-C bond formation via 1,2-migration of an aryl group
    Egami, Hiromichi
    Shimizu, Ryo
    Usui, Yoshihiko
    Sodeoka, Mikiko
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (66) : 7346 - 7348
  • [9] Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines
    Egami, Hiromichi
    Kawamura, Shintaro
    Miyazaki, Ayako
    Sodeoka, Mikiko
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (30) : 7841 - 7844
  • [10] Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles
    Egami, Hiromichi
    Shimizu, Ryo
    Kawamura, Shintaro
    Sodeoka, Mikiko
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) : 4000 - 4003