Palladium-Catalysed Synthesis of α-(Trifluoromethyl)styrenes by Means of Directed C-H Bond Functionalization

被引:19
|
作者
Zhao, Qun [2 ]
Besset, Tatiana [2 ]
Poisson, Thomas [2 ]
Bouillon, Jean-Philippe [1 ,2 ]
Pannecoucke, Xavier [2 ]
机构
[1] Normandie Univ, COBRA, UMR 6014, F-76821 Mont St Aignan, France
[2] Univ Rouen, INSA Rouen, CNRS, F-76821 Mont St Aignan, France
关键词
Synthetic methods; Fluorine; C-H activation; Palladium; Homogeneous catalysis; ALPHA-TRIFLUOROMETHYLSTYRENE DERIVATIVES; MEDICINAL CHEMISTRY; ORTHO-ARYLATION; ARYL HALIDES; FLUORINE; ALKENES; ARENES; 2-BROMO-3,3,3-TRIFLUOROPROPENE; TRIFLUOROMETHYLTHIOLATION; DIFLUOROACETYLATION;
D O I
10.1002/ejoc.201501217
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report the first introduction of 2-bromo-3,3,3-trifluoropropene (BTP) by directed C-H bond functionalization. The developed method gives straightforward access to -(trifluoromethyl)styrene derivatives without prior prefunctionalization of the substrates. This palladium-catalysed transformation was applied to a broad range of substrates, and the corresponding trifluoromethylated products were obtained in good yields. This approach represents an alternative pathway to the classical method previously used to access such molecules.
引用
收藏
页码:76 / 82
页数:7
相关论文
共 50 条
  • [1] Palladium-Catalysed, Directed C-H Coupling with Organometallics
    Giri, Ramesh
    Thapa, Surendra
    Kafle, Arjun
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) : 1395 - 1411
  • [2] Palladium-catalysed transannular C-H functionalization of alicyclic amines
    Topczewski, Joseph J.
    Cabrera, Pablo J.
    Saper, Noam I.
    Sanford, Melanie S.
    NATURE, 2016, 531 (7593) : 220 - 224
  • [3] Recent Developments in Palladium-Catalysed Non-Directed C-H Bond Activation in Arenes
    Kancherla, Sindhu
    Jorgensen, Kare B.
    Fernandez-Ibanez, M. Angeles
    SYNTHESIS-STUTTGART, 2019, 51 (03): : 643 - 663
  • [4] Palladium-catalysed norbornene-mediated C-H functionalization of arenes
    Ye, Juntao
    Lautens, Mark
    NATURE CHEMISTRY, 2015, 7 (11) : 863 - 870
  • [5] Palladium-Catalyzed Synthesis of 3-Trifluoromethyl-Substituted 1,3-Butadienes by Means of Directed C-H Bond Functionalization
    Zhao, Qun
    Tognetti, Vincent
    Joubert, Laurent
    Besset, Tatiana
    Pannecoucke, Xavier
    Bouillon, Jean-Philippe
    Poisson, Thomas
    ORGANIC LETTERS, 2017, 19 (08) : 2106 - 2109
  • [6] Oxindole synthesis by palladium-catalysed aromatic C-H alkenylation
    Ueda, Satoshi
    Okada, Takahiro
    Nagasawa, Hideko
    CHEMICAL COMMUNICATIONS, 2010, 46 (14) : 2462 - 2464
  • [7] Enantioselective amine α-functionalization via palladium-catalysed C-H arylation of thioamides
    Jain, Pankaj
    Verma, Pritha
    Xia, Guoqin
    Yu, Jin-Quan
    NATURE CHEMISTRY, 2017, 9 (02) : 140 - 144
  • [8] Greener solvents for ruthenium and palladium-catalysed aromatic C-H bond functionalisation
    Fischmeister, Cedric
    Doucet, Henri
    GREEN CHEMISTRY, 2011, 13 (04) : 741 - 753
  • [9] Synthesis of Dibenzofurans by Palladium-Catalysed Tandem Denitrification/C-H Activation
    Du, Zhenting
    Zhou, Jing
    Si, Changmei
    Ma, Weili
    SYNLETT, 2011, (20) : 3023 - 3025
  • [10] Benzazetidine synthesis via palladium-catalysed intramolecular C-H amination
    He, Gang
    Lu, Gang
    Guo, Zhengwei
    Liu, Peng
    Chen, Gong
    NATURE CHEMISTRY, 2016, 8 (12) : 1131 - 1136