Recent advances in C-F bond activation of trifluoromethylated carbonyl compounds and derivatives

被引:18
|
作者
Gong, Xuanming [1 ]
Zhou, Qin [1 ]
Yan, Guobing [1 ]
机构
[1] Zhejiang A&F Univ, Coll Jiyang, Zhuji 311800, Peoples R China
关键词
TRIFLUOROACETIC-ACID; ELECTROREDUCTIVE DEFLUORINATION; H TRIFLUOROMETHYLATION; N-TOSYLHYDRAZONES; DIAZO-COMPOUNDS; RECENT PROGRESS; SILYL ETHERS; FLUORINE; KETONES; GENERATION;
D O I
10.1039/d2ob00795a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The selective activation of inert C-F bonds is one of the most challenging topics in modern organic chemistry. Trifluoromethylketones represent a class of versatile building blocks that are inexpensive and readily available polyfluorinated starting materials. The functionalization of C-F bond in trifluoromethylketones has recently been achieved using difluoroenolates, difluorinated acyl anions or radicals for the synthesis of difluoromethylene compounds. This strategy has also been successfully applied to their derivatives, such as trifluoromethylated esters, amides, diazo compounds and N-sulfonylhydrazones, which would be of significant value for the synthesis of partially fluorinated intermediates. In this review, we mainly focus on the recent advances, challenges and perspectives of trifluoromethylated carbonyl compounds and their derivatives via C-F bond activation, along with mechanistic insight.
引用
收藏
页码:5365 / 5376
页数:12
相关论文
共 50 条
  • [21] Synthesis and structure of rhodium(I) silyl carbonyl complexes: photochemical C-F and C-H bond activation of fluorinated aromatic compounds
    Zamostna, Lada
    Sander, Stefan
    Braun, Thomas
    Laubenstein, Reik
    Braun, Beatrice
    Herrmann, Roy
    Klaering, Paul
    DALTON TRANSACTIONS, 2015, 44 (20) : 9450 - 9469
  • [22] BIOLOGICAL PROPERTIES OF COMPOUNDS CONTAINING C-F BOND
    SMITH, FA
    CHEMTECH, 1973, (JUL) : 422 - 429
  • [23] Catalytic C-F bond activation of nonactivated monofluoroarenes
    Young, RJ
    Grushin, VV
    ORGANOMETALLICS, 1999, 18 (03) : 294 - 296
  • [24] Consecutive C-F Bond Activation of Hexafluorobenzene and Decafluorobiphenyl
    Schaub, Thomas
    Fischer, Peter
    Meins, Thomas
    Radius, Udo
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2011, (20) : 3122 - 3126
  • [25] BIOCHEMICAL ASPECTS OF COMPOUNDS CONTAINING C-F BOND
    SMITH, FA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1971, (NSEP): : 22 - &
  • [26] Trifluoromethyl coordination and C-F bond activation at calcium
    Barrett, Anthony G. M.
    Crimmin, Mark R.
    Hill, Michael S.
    Hitchcock, Peter B.
    Procopiou, Panayiotis A.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (33) : 6339 - 6342
  • [27] Aliphatic C-F bond activation at room temperature
    不详
    CHEMICAL & ENGINEERING NEWS, 2005, 83 (11) : 33 - 33
  • [28] C-F bond activation by transient phosphenium dications
    Vidovic, Dragoslav
    Dordevic, Nenanja
    Tay, Madelyn Qin Yi
    Dimic, Dusan
    Muthaiah, Senthilkumar
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [29] C-F Bond Activation by Transient Phosphenium Dications
    Dordevic, Nemanja
    Tay, Madelyn Qin Yi
    Muthaiah, Senthilkumar
    Ganguly, Rakesh
    Dimic, Dusan
    Vidovic, Dragoslav
    INORGANIC CHEMISTRY, 2015, 54 (09) : 4180 - 4182
  • [30] Desymmetrization of difluoromethylene groups by C-F bond activation
    Butcher, Trevor W.
    Yang, Jonathan L.
    Amberg, Willi M.
    Watkins, Nicholas B.
    Wilkinson, Natalie D.
    Hartwig, John F.
    NATURE, 2020, 583 (7817) : 548 - +