Transition-metal-free synthesis of β-trifluoromethylated enamines with trifluoromethanesulfinate

被引:42
|
作者
Jiang, Huanfeng [1 ]
Huang, Wei [1 ]
Yu, Yue [1 ]
Yi, Songjian [1 ]
Li, Jiawei [1 ]
Wu, Wanqing [1 ]
机构
[1] South China Univ Technol, Key Lab Funct Mol Engn Guangdong Prov, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
COPPER-CATALYZED TRIFLUOROMETHYLATION; ALPHA; BETA-UNSATURATED CARBOXYLIC-ACIDS; LIGHT PHOTOREDOX CATALYSIS; C BOND FORMATION; OXIDATIVE TRIFLUOROMETHYLATION; ROOM-TEMPERATURE; SODIUM TRIFLUOROMETHANESULFINATE; MEDICINAL CHEMISTRY; POLYSUBSTITUTED PYRROLES; HETEROAROMATIC-COMPOUNDS;
D O I
10.1039/c7cc03125d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have developed a transition-metal free trifluoromethylation protocol between enamines and CF3SO2Na. A wide range of beta-trifluoromethyl substituted enamines were delivered in moderate to high yields with only E-configurations.
引用
收藏
页码:7473 / 7476
页数:4
相关论文
共 50 条
  • [1] Transition-Metal-Free Trifluoromethylation of Aldehyde Derivatives with Sodium Trifluoromethanesulfinate
    Tan, Zheng
    Zhang, Shiwei
    Zhang, Yan
    Li, Yunpeng
    Ni, Minjie
    Feng, Bainian
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18): : 9384 - 9399
  • [2] Transition-metal-free oxidative trifluoromethylation of unsymmetrical biaryls with trifluoromethanesulfinate
    Yang, Yu-Dong
    Iwamoto, Kanji
    Tokunaga, Etsuko
    Shibata, Norio
    CHEMICAL COMMUNICATIONS, 2013, 49 (48) : 5510 - 5512
  • [3] Transition-metal-free electrophilic trifluoromethylthiolation with sodium trifluoromethanesulfinate at room temperature
    Bu, Mei-jie
    Lu, Guo-ping
    Cai, Chun
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (02): : 266 - 270
  • [4] Transition-Metal-Free Synthesis of Pyridine Derivatives by Thermal Cyclization of N -Propargyl Enamines
    Chikayuki, Yuya
    Miyashige, Takakane
    Yonekawa, Shiori
    Kirita, Akiko
    Matsuo, Natsuko
    Teramoto, Hiroyoshi
    Sasaki, Shigeru
    Higashiyama, Kimio
    Yamauchi, Takayasu
    SYNTHESIS-STUTTGART, 2020, 52 (07): : 1113 - 1121
  • [5] Facile Synthesis of Sulfonyl Amidines and β-Amino Sulfonyl Enamines under Transition-Metal-Free Conditions
    Gao, Tingting
    Zhao, Mingming
    Meng, Xu
    Li, Chuanbin
    Chen, Baohua
    SYNLETT, 2011, (09) : 1281 - 1284
  • [6] Synthesis of Trifluoromethylated Cycloheptatrienes from N-Tosylhydrazones: Transition-Metal-Free Buchner Ring Expansion
    Zhang, Zhikun
    Feng, Jiajie
    Xu, Yan
    Zhang, Songnan
    Ye, Yuxuan
    Li, Tianjiao
    Wang, Xi
    Chen, Jun
    Zhang, Yan
    Wang, Jianbo
    SYNLETT, 2015, 26 (01) : 59 - 62
  • [7] A Transition-Metal-Free Synthesis of Fluorinated Naphthols
    Hammann, Jeffrey M.
    Unzner, Teresa A.
    Magauer, Thomas
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (22) : 6733 - 6738
  • [8] Transition-metal-free synthesis of substituted aminocyclopropanes
    Cyr, Patrick
    Cote-Raiche, Alexandre
    Bronner, Sarah
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [9] A Transition-Metal-Free Synthesis of Multisubstituted Imidazoles
    Wu, Ping
    Zhang, Lutao
    Zhang, Xueguo
    Guo, Xin
    Chen, Baohua
    CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (04) : 363 - 367
  • [10] Transition-Metal-Free Synthesis of Tertiary Aminocyclopropanes
    Cyr, Patrick
    Cote-Raiche, Alexandre
    Bronner, Sarah M.
    ORGANIC LETTERS, 2016, 18 (24) : 6448 - 6451