β-Trifluoromethyl α,β-unsaturated Ketones: Efficient Building Blocks for Diverse Trifluoromethylated Molecules

被引:39
|
作者
Chaudhary, Bharatkumar [1 ]
Kulkarni, Neeraj [1 ]
Saiyed, Nehanaz [1 ]
Chaurasia, Meenakshi [1 ]
Desai, Surbhi [1 ]
Potkule, Sagar [1 ]
Sharma, Satyasheel [2 ]
机构
[1] Ahmedabad NIPER A, Dept Med Chem, Natl Inst Pharmaceut Educ & Res, Gandhinagar 382355, Gujarat, India
[2] Ahmedabad NIPER A, Dept Nat Prod, Natl Inst Pharmaceut Educ & Res, Gandhinagar 382355, Gujarat, India
关键词
Trifluoromethyl group; Fluorinated building blocks; Enones; Conjugate addition; Trifluoromethylated heterocycles; ASYMMETRIC MICHAEL ADDITION; ELECTRON-DEFICIENT ALKENES; ENANTIOSELECTIVE 3+2 CYCLOADDITIONS; FRIEDEL-CRAFTS ALKYLATION; THIOCARBONYL S-METHANIDES; RAUHUT-CURRIER REACTION; CARBON CENTER BEARING; STEREOSELECTIVE-SYNTHESIS; ONE-POT; BETA-TRIFLUOROMETHYL-ALPHA; BETA-UNSATURATED KETONES;
D O I
10.1002/adsc.202001018
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The trifluoromethyl (CF3) group is an advantageous structural motif in various biologically active molecules as well as materials, which is depicted by steadily increasing demand from the industries involved in drug discovery, agrochemicals and material development. beta-trifluoromethyl alpha,beta-unsaturated carbonyl compounds constitute a very efficient building blocks as starting material in the synthesis of fluorinated molecules. Their usage for the synthesis of various heterocycles and organic molecules bearing stereogenic carbon containing CF3 motif has received significant attention during the recent times. This review provides the existing methods for the synthesis of beta-substituted trifluoromethyl-alpha,beta-unsaturated ketones and the efforts made by researchers for the synthetic development through various reactions by employing them as synthetic building blocks for trifluoromethylated organic scaffolds.
引用
收藏
页码:4794 / 4819
页数:26
相关论文
共 50 条
  • [31] Synthesis of trifluoromethyl derivatives of pyrrole.: Reaction of α,β-unsaturated trifluoromethyl ketones with sodium cyanide
    Nenajdenko, VG
    Druzhinin, SV
    Balenkova, ES
    RUSSIAN CHEMICAL BULLETIN, 2003, 52 (11) : 2467 - 2472
  • [32] Synthesis of trifluoromethyl derivatives of pyrrole. Reaction of α,β-unsaturated trifluoromethyl ketones with sodium cyanide
    V. G. Nenajdenko
    S. V. Druzhinin
    E. S. Balenkova
    Russian Chemical Bulletin, 2003, 52 : 2467 - 2472
  • [33] Synthesis of Trifluoromethyl Tetrafluoro-6-sulfanyl-Substituted Alkenes, Ketones, and Acids: Polar Hydrophobic Building Blocks
    Ikeda, Akari
    Zhong, Linbin
    Savoie, Paul R.
    von Hahmann, Cortney N.
    Zheng, Wei
    Welch, John T.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (06) : 772 - 780
  • [34] Methods for the synthesis of α,β-unsaturated trifluoromethyl ketones and their use in organic synthesis
    Nenaidenko, V.G.
    Sanin, A.V.
    Balenkova, E.S.
    Uspekhi Khimii, 68 (06): : 504 - 505
  • [35] Methods for the synthesis of α,β-unsaturated trifluoromethyl ketones and their use in organic synthesis
    Nenaidenko, VG
    Sanin, AV
    Balenkova, ES
    USPEKHI KHIMII, 1999, 68 (06) : 483 - 505
  • [36] A new sequential defluorination route to α-fluoro-α,β-unsaturated ketones from trifluoromethyl ketones
    Hata, H
    Kobayashi, T
    Amii, H
    Uneyama, K
    Welch, JT
    TETRAHEDRON LETTERS, 2002, 43 (35) : 6099 - 6102
  • [37] EFFICIENT CONVERSION OF KETONES TO ALPHA-UNSATURATED,BETA-UNSATURATED KETONES
    ABDULLA, RF
    FUHR, KH
    JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21): : 4248 - 4250
  • [38] Visible light induced Trifluoromethyl Migration: Easy Access to α-Trifluoromethylated Ketones from Enol Triflates
    Liu, Shuyang
    Jie, Jiyang
    Yu, Jipan
    Yang, Xiaobo
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (02) : 267 - 271
  • [39] TRIFLUOROMETHYL KETONES FROM CARBOXYLIC-ACIDS .2. A VERSATILE ACCESS TO TRIFLUOROMETHYLATED HETEROCYCLES
    BOIVIN, J
    ELKAIM, L
    ZARD, SZ
    TETRAHEDRON, 1995, 51 (09) : 2585 - 2592
  • [40] One-pot relay reduction-isomerization of β-trifluoromethylated-α, β-unsaturated ketones to chiral β-trifluoromethylated saturated ketones over combined catalysts in aqueous medium
    Xia, Xuelin
    Wu, Meng
    Jin, Ronghua
    Cheng, Tanyu
    Liu, Guohua
    GREEN CHEMISTRY, 2015, 17 (07) : 3916 - 3922