Metal-Free Three-Component Regioselective Aminofluorination of Styrene Derivatives

被引:30
|
作者
Zhang, Qiao [1 ]
Zheng, Guangfan [1 ]
Zhang, Qian [1 ]
Li, Yan [1 ]
Zheng, Qan [1 ]
机构
[1] Northeast Normal Univ, Dept Chem, Key Lab Funct Organ Mol Design & Synth Jilin Prov, 5268 Renmin Rd, Changchun 130024, Jilin, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 15期
基金
中国国家自然科学基金;
关键词
UNACTIVATED ALKENES; AQUEOUS-SOLUTION; INTRAMOLECULAR AMINOFLUORINATION; INTERMOLECULAR AMINOFLUORINATION; OLEFIN AMINOFLUORINATION; MEDICINAL CHEMISTRY; FLUORINATION; CARBOFLUORINATION; AMINATION; ALKYNES;
D O I
10.1021/acs.joc.7b01089
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first metal-free, three-component radical aminofluorination of styrene derivatives has been developed, which employs Selectfluor as a fluorine source and azole derivatives as a nitrogen source. This transformation proceeds with high regioselectivity, providing various 1,2-aminofluorination compounds under mild conditions. Mechanistic studies suggest that the aminofluorination process might involve radical fluorination followed by nucleophilic amination.
引用
收藏
页码:8258 / 8266
页数:9
相关论文
共 50 条
  • [41] Photoinduced Copper-Catalyzed Three-Component Radical Carboamination of Styrene Derivatives
    Huan, Xiao-Die
    Zhang, Juan
    Xiao, Wen-Jing
    Chen, Jia-Rong
    CHEMCATCHEM, 2024, 16 (23)
  • [42] Metal-free synthesis of quinoline-2,4-dicarboxylate derivatives using aryl amines and acetylenedicarboxylates through a pseudo three-component reaction
    Ali, Saghir
    Khan, Abu T.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (32) : 7041 - 7050
  • [43] Metal-free three-component tandem cyclization for modular synthesis of 2,3-dihydrobenzothiazin-4-ones
    Zhang, Guan
    Wan, Huimin
    Dong, Na
    Zhu, Antong
    Zhou, Yao
    Song, Qiuling
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (07): : 2021 - 2026
  • [44] A green and metal-free one-pot three-component synthesis of thiazolobenzimidazoles in sustainable deep eutectic solvent
    Verma, Ankit
    Sahay, Suhag S.
    Nayak, Sushree S.
    Bhagat, Shivani
    Dani, Shilpa H.
    Nayak, Bhojkumar
    Pratap, Umesh R.
    INORGANIC CHEMISTRY COMMUNICATIONS, 2024, 166
  • [45] Metal-free synthesis of alkynyl alkyl selenides via three-component coupling of terminal alkynes, Se, and epoxides
    Wu, Ge
    Min, Lin
    Li, Hongchen
    Gao, Wenxia
    Ding, Jinchang
    Huang, Xiaobo
    Liu, Miaochang
    Wu, Huayue
    GREEN CHEMISTRY, 2018, 20 (07) : 1560 - 1563
  • [46] Transition metal-free regioselective direct acylation of quinazolines for the synthesis of acylquinazoline derivatives
    Chen, Wei
    Fang, Jingjun
    Huang, Jian
    Yang, Qin
    Song, Zhibin
    Ding, Qiuping
    Wang, Hongming
    Peng, Yiyuan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (42) : 8603 - 8616
  • [47] Metal-free chemo- and regioselective acylation of pyridine derivatives with alcohols in water
    Kianmehr, Ebrahim
    Pakbaznia, Azin
    Faghih, Nasser
    Forournadi, Alireza
    TETRAHEDRON, 2017, 73 (11) : 1407 - 1412
  • [48] Pyrromethene Derivatives in Three-Component Photoinitiating Systems for Free Radical Photopolymerization
    Tarzi, O. I.
    Allonas, X.
    Ley, C.
    Fouassier, J. -P.
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2010, 48 (12) : 2594 - 2603
  • [49] A Catalytic Three-Component Aminofluorination of Unactivated Alkenes with Electron-Rich Amino Sources
    Dong, Junchao
    Liang, Yujie
    Li, Yang
    Guan, Wei
    Zhang, Qian
    Fu, Junkai
    ADVANCED SCIENCE, 2024, 11 (12)
  • [50] Catalyst free, regioselective one-pot three-component synthesis of thiazol-2-imine derivatives in ionic liquid
    Kumar, G. Santosh
    Ragini, S. Pushpa
    Meshram, H. M.
    TETRAHEDRON LETTERS, 2013, 54 (45) : 5974 - 5978