Transition metal-free electrochemical fluorotrifluoromethylation of Styrenes

被引:9
|
作者
Lu, Yi [1 ]
Liu, Zhirui [1 ]
Liu, Chao [1 ]
Wu, Yunpeng [1 ]
Li, Lu [1 ]
Liu, Siyuan [1 ]
Wang, Hong [1 ]
Gao, Wei [1 ]
Liu, Zhenxian [2 ]
Chen, Jianbin [1 ,2 ]
机构
[1] Qilu Univ Technol, Shandong Acad Sci, Sch Chem & Chem Engn, Shandong Prov Key Lab Mol Engn,State Key Lab Bioba, Jinan 250353, Peoples R China
[2] Qilu Univ Technol, Shandong Acad Sci, Intellectual Property Operat Management Off, Jinan 250353, Peoples R China
基金
中国国家自然科学基金;
关键词
FLUORINATION; ALKENES; TRIFLUOROMETHYLATION;
D O I
10.1039/d2qo01947g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An environmentally friendly electrochemical fluorotrifluoromethylation of styrenes was developed via the tandem processes of electro-oxidation and radical and nucleophilic addition. By using commercial CF3SO2Na and Et3N center dot 3HF as the CF3 and F sources, respectively, a series of potentially bio-active multi-site F-containing compounds were obtained in moderate to good yields. This fluorotrifluoromethylation strategy is catalyst- and oxidant-free, and demonstrates mild conditions and high step economy features. In addition, several analytical methods, including cyclic voltammetry and control experiments, were conducted to investigate a reasonable reaction mechanism.
引用
收藏
页码:1283 / 1288
页数:6
相关论文
共 50 条
  • [41] Transition metal-free strategies for the stereoselective construction of spirocyclopropyl oxindoles
    Bacher, Emily P.
    Ashfeld, Brandon L.
    TETRAHEDRON, 2020, 76 (04)
  • [42] Transition Metal-Free Approach to Propynenitriles and 3-Chloropropenenitriles
    Sharma, Pawan K.
    Ram, Sita
    Chandak, Navneet
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (06) : 894 - 899
  • [43] Fast and transition metal-free general method for the preparation of chalcogenophosphates
    Wang, Junxing
    Wang, Xiaolong
    Li, Hongjie
    Yan, Jie
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 859 : 75 - 79
  • [44] Transition Metal-free Trifluoroethoxylation of Diaryliodonium Salts and Fluoro Alcohols
    Li, Jian
    Wang, Zhengbing
    Lu, Xuechen
    Lin, Jing
    Liu, Li
    Zhao, Yue
    LETTERS IN ORGANIC CHEMISTRY, 2019, 16 (06) : 485 - 490
  • [45] Advances in the Transition Metal-Free C-H Trifluoromethylation
    Chen, Demao
    Jiang, Jianwen
    Wan, Jie-Ping
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (21) : 2582 - 2594
  • [46] Transition Metal-Free Tryptophan-Selective Bioconjugation of Proteins
    Seki, Yohei
    Ishiyama, Takashi
    Sasaki, Daisuke
    Abe, Junpei
    Sohma, Youhei
    Oisaki, Kounosuke
    Kanai, Motomu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (34) : 10798 - 10801
  • [47] Transition Metal-free Photoorganocatalytic Fluoroalkylation Reactions of Organic Compounds
    Barata-Vallejo, Sebastian
    Yerien, Damian E.
    Lantano, Beatriz
    Postigo, Al
    CURRENT ORGANIC CHEMISTRY, 2016, 20 (27) : 2838 - 2847
  • [48] Designing Metal-Free Catalysts by Mimicking Transition-Metal Pincer Templates
    Lu, Gang
    Li, Haixia
    Zhao, Lili
    Huang, Fang
    Schleyer, Paul von Rague
    Wang, Zhi-Xiang
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (07) : 2038 - 2043
  • [49] Metal-free photocleavage of the C(non-acyl)-S bond of thioesters for regioselective pyridylthioesterification of styrenes
    Wu, Qi
    Zhao, You-Hui
    Chai Lu-Lu
    Li, Hai-Yan
    Li, Hong-Xi
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (11) : 2977 - 2985
  • [50] Deaminative carbonylative coupling of alkylamines with styrenes under transition-metal-free conditions
    Zhao, Fengqian
    Li, Chong-Liang
    Wu, Xiao-Feng
    CHEMICAL COMMUNICATIONS, 2020, 56 (64) : 9182 - 9185