Copper-catalyzed α-selective C–H trifluoromethylation of acrylamides with TMSCF3

被引：1
|
作者：
Shang-Zheng Sun [1 ]
Hui Xu [2 ]
Hui-Xiong Dai [2 ]
机构：
[1] Department of Chemistry, Innovative Drug Research Center, Shanghai University
[2] Department of Medicinal Chemistry, Shanghai Institute of Materia Medica, University of Chinese Academy of Sciences, Chinese Academy of Sciences
来源：
Chinese Chemical Letters | 2019年 / 30卷 / 05期
基金：
中国国家自然科学基金;
关键词：
α-Selectivity; C–H trifluoromethylation; Copper; Acrylamides; Heterocycle;
D O I：
暂无
中图分类号：
O621.251 [];
学科分类号：
070303 ; 081704 ;
摘要：
A copper-catalyzed α-selective C–H trifluoromethylation of acrylamides with TMSCF3is described. A wide range of arenes and heteroarenes at the β-position of acrylamides are compatible with the reaction,affording the corresponding(E)-trifluoromethylated products in moderate to good yields. The reaction proceeded fast and can be completed within 30 min.
引用
收藏
页码：969 / 972
页数：4
相关论文
共 50 条
  • [41] Copper-catalyzed nucleophilic trifluoromethylation of benzylic chlorides
    Miyake, Yoshihiro
    Ota, Shin-ichi
    Shibata, Masashi
    Nakajima, Kazunari
    Nishibayashi, Yoshiaki
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (30) : 5594 - 5596
  • [42] Development and Challenges in the Copper-Catalyzed Trifluoromethylation of Alkenes
    Liu, Xiaowu
    Wu, Xiaoxing
    SYNLETT, 2013, 24 (15) : 1882 - 1886
  • [43] Copper-catalyzed nucleophilic trifluoromethylation of propargylic halides
    Miyake, Yoshihiro
    Ota, Shin-ichi
    Shibata, Masashi
    Nakajima, Kazunari
    Nishibayashi, Yoshiaki
    CHEMICAL COMMUNICATIONS, 2013, 49 (71) : 7809 - 7811
  • [44] Copper-mediated pentafluoroethylation of organoboronates and terminal alkynes with TMSCF3
    Pan, Shitao
    Xie, Qiqiang
    Wang, Xiu
    Wang, Qian
    Ni, Chuanfa
    Hu, Jinbo
    CHEMICAL COMMUNICATIONS, 2022, 58 (33) : 5156 - 5159
  • [45] Copper-Catalyzed Oxidative Benzylarylation of Acrylamides by Benzylic C-H Bond Functionalization for the Synthesis of Oxindoles
    Zhou, Shi-Liu
    Guo, Li-Na
    Wang, Hua
    Duan, Xin-Hua
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (39) : 12970 - 12973
  • [46] Copper-catalyzed trifluoromethylation of arylsulfinate salts using an electrophilic trifluoromethylation reagent
    Lin, Xiaoxi
    Wang, Guimei
    Li, Huaifeng
    Huang, Yuanyuan
    He, Weiming
    Ye, Dandan
    Huang, Kuo-Wei
    Yuan, Yaofeng
    Weng, Zhiqiang
    TETRAHEDRON, 2013, 69 (12) : 2628 - 2632
  • [47] Copper-catalyzed Z-selective synthesis of acrylamides and polyacrylamides via alkylidene ketenimines
    Duan, Xuelun
    Zheng, Nan
    Li, Ming
    Liu, Gongbo
    Sun, Xinhao
    Wu, Qiming
    Song, Wangze
    NATURE COMMUNICATIONS, 2022, 13 (01)
  • [48] C(sp2)-H Trifluoromethylation of enamides using TMSCF3: access to trifluoromethylated isoindolinones, isoquinolinones, 2-pyridinones and other heterocycles
    Krishnamurti, Vinayak
    Munoz, Socrates B.
    Ispizua-Rodriguez, Xanath
    Vickerman, Jeffrey
    Mathew, Thomas
    Surya Prakash, G. K.
    CHEMICAL COMMUNICATIONS, 2018, 54 (75) : 10574 - 10577
  • [49] Copper-catalyzed Z-selective synthesis of acrylamides and polyacrylamides via alkylidene ketenimines
    Xuelun Duan
    Nan Zheng
    Ming Li
    Gongbo Liu
    Xinhao Sun
    Qiming Wu
    Wangze Song
    Nature Communications, 13
  • [50] Copper-Catalyzed C4-H Regioselective Phosphorylation/Trifluoromethylation of Free 1-Naphthylamines
    Jing, Chunfeng
    Chen, Xiaolan
    Sun, Kai
    Yang, Yongkang
    Chen, Tong
    Liu, Yan
    Qu, Lingbo
    Zhao, Yufen
    Yu, Bing
    ORGANIC LETTERS, 2019, 21 (02) : 486 - 489
12345