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
  • [1] Metal-Free Three-Component Oxyalkynylation of Alkenes
    Li, Yangshan
    Lu, Ran
    Sun, Shutao
    Liu, Lei
    ORGANIC LETTERS, 2018, 20 (21) : 6836 - 6839
  • [2] Three-Component Metal-Free Arylation of Isocyanides
    Basavanag, Unnamatla M. V.
    Dos Santos, Aurelie
    El Kaim, Laurent
    Gamez-Montano, Rocio
    Grimaud, Laurence
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (28) : 7194 - 7197
  • [3] Metal-free aminofluorination and diamination of alkenes
    Liskin, Dmitry V.
    Michael, Forrest E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [4] Metal-Free Decarboxylative Three-Component Coupling Reaction for the Synthesis of Propargylamines
    Park, Kyungho
    Heo, Yumi
    Lee, Sunwoo
    ORGANIC LETTERS, 2013, 15 (13) : 3322 - 3325
  • [5] Chemoselective three-component synthesis of α-carbolines under metal-free conditions
    Feng, Wei
    Zhang, Chao
    Zhou, Xinlin
    You, Kuiyi
    Deng, Guo-Jun
    Chen, Shanping
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (21) : 5457 - 5462
  • [6] A three-component approach to isoxazolines and isoxazoles under metal-free conditions
    Wang, Dahan
    Zhang, Feng
    Xiao, Fuhong
    Deng, Guo-Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (41) : 9163 - 9168
  • [7] Metal-Free Three-Component Domino Approach to Phosphonylated Triazolines and Triazoles
    Ahamad, Shakir
    Kant, Ruchir
    Mohanan, Kishor
    ORGANIC LETTERS, 2016, 18 (02) : 280 - 283
  • [8] Metal-free three-component amino- and carbotrideuteromethylthiolation of alkenes in water
    Han, Siyu
    Zhao, Lin
    Zhou, Xinyu
    Zhang, Kemeng
    Ma, Yunfei
    Wu, Ge
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (21): : 6064 - 6068
  • [9] Transition metal-free aminofluorination of ß,γ-unsaturated hydrazones: base-controlled regioselective synthesis of fluorinated dihydropyrazole and tetrahydropyridazine derivatives
    Zhao, Juan
    Jiang, Min
    Liu, Jin-Tao
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (07): : 1155 - 1159
  • [10] An Efficient Synthesis of α-Sulfonamide Phosphonates through Metal-Free Three-Component Reaction
    Ramani, Arti
    Bhavyesh, Desai
    Kanta Koppolu, Mani
    Chinna Ashalu, Kashamalla
    Begari, Eeshwaraiah
    Naveen, Togati
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 13 (07)