Continuous flow palladium-catalyzed trifluoromethylthiolation of C-H bonds

被引:12
|
作者
Bouchard, Alexanne [1 ,2 ]
Kairouz, Vanessa [1 ,2 ]
Manneveau, Maxime [3 ]
Xiong, Heng-Ying [3 ]
Besset, Tatiana [3 ]
Pannecoucke, Xavier [3 ]
Lebel, Helene [1 ,2 ]
机构
[1] Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada
[2] Univ Montreal, Continuous Flow Synth Lab, POB 6128, Montreal, PQ, Canada
[3] Normandie Univ, INSA Rouen, CNRS, UNIROUEN,COBRA,UMR 6014, F-76000 Rouen, France
基金
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词
Aminoquinoline; Bidentate directing group; C-SCF3; bond; Organofluorine compounds; Flow process; C-H activation; Halogenation; Trifluoromethylthioethers; FUNCTIONALIZATION; ACTIVATION;
D O I
10.1007/s41981-018-0023-4
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A continuous flow process for the synthesis of trifluoromethylthioethers is reported. The palladium-catalyzed C-H trifluoromethylthiolation of amides derived from the 8-aminoquinoline using N-[(trifluoromethyl)thio]phthalimide produced the desired products in moderate to good yields with a residence time of 20 min. In comparison with the batch process, the reaction time was decreased by a factor of 100 to 200, demonstrating the positive effect of continuous flow processes for this type of reaction.
引用
收藏
页码:9 / 12
页数:4
相关论文
共 50 条
  • [21] Palladium-Catalyzed C-C Bonds Formation Reactions via Selective C-H Bonds Functionalization
    Li Hu
    Shi Zhangjie
    PROGRESS IN CHEMISTRY, 2010, 22 (07) : 1414 - 1433
  • [22] PALLADIUM-CATALYZED ARYLATION AT C-H AND C-C BONDS OF MASKED THIAZOLE DERIVATIVES
    Furukawa, Hirotoshi
    Matsumura, Suguru
    Sugie, Atsushi
    Monguchi, Daiki
    Mori, Atsunori
    HETEROCYCLES, 2009, 79 : 303 - 309
  • [23] Palladium-Catalyzed C-H Perfluoroalkylation of Arenes
    Loy, Rebecca N.
    Sanford, Melanie S.
    ORGANIC LETTERS, 2011, 13 (10) : 2548 - 2551
  • [24] Palladium-Catalyzed C-H Acetoxylation Reations
    Chen, Tianbao
    Zhang, Ming
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (04) : 813 - 826
  • [25] Palladium-Catalyzed Allylic C-H Fluorination
    Braun, Marie-Gabrielle
    Doyle, Abigail G.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) : 12990 - 12993
  • [26] The Cross-Selectivity in Palladium-Catalyzed Coupling of Simple Aryl C-H Bonds
    Lu, Wenjun
    SYNLETT, 2025, 36 (06) : 644 - 650
  • [27] Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions
    Giri, R
    Chen, X
    Yu, JQ
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (14) : 2112 - 2115
  • [28] Palladium-Catalyzed Aryl C-H Bonds Activation/Acetoxylation Utilizing a Bidentate System
    Gou, Fa-Rong
    Wang, Xiang-Chuan
    Huo, Peng-Fei
    Bi, Hai-Peng
    Guan, Zheng-Hui
    Liang, Yong-Min
    ORGANIC LETTERS, 2009, 11 (24) : 5726 - 5729
  • [29] From Anilines to Isatins: Oxidative Palladium-Catalyzed Double Carbonylation of C-H Bonds
    Li, Wu
    Duan, Zhengli
    Zhang, Xueye
    Zhang, Heng
    Wang, Mengfan
    Jiang, Ru
    Zeng, Hongyao
    Liu, Chao
    Lei, Aiwen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (06) : 1893 - 1896
  • [30] Palladium-catalyzed enantioselective C-H functionalization via C-H palladation
    Zhan, Bei-Bei
    Jin, Liang
    Shi, Bing-Feng
    TRENDS IN CHEMISTRY, 2022, 4 (03): : 220 - 235