Metal-free trifluoroethylation of activated alkenes: rapid access to construct fluorinated 3,3-disubstituted 2-oxindoles

被引：18
|
作者：
Mai, Wen-Peng [1 ]
Sun, Bin [1 ]
Qian, Guan-Sheng [2 ]
Yuan, Jin-Wei [1 ]
Mao, Pu [1 ]
Yang, Liang-Ru [1 ]
Xiao, Yong-Mei [1 ]
机构：
[1] Henan Univ Technol, Sch Chem & Chem Engn, Zhengzhou 450001, Henan, Peoples R China
[2] South Cent Univ Nationalities, Coll Chem & Mat Sci, Wuhan 430074, Peoples R China
来源：
TETRAHEDRON | 2015年 / 71卷 / 44期
基金：
中国国家自然科学基金;
关键词：
Metal-free; C-H functionalization; Fluorination; Radical; Cyclization; RADICAL TANDEM CYCLIZATION; N-ARYLACRYLAMIDES; CF3-CONTAINING OXINDOLES; GENERAL-METHODS; TRIFLUOROMETHYLATION; BOND; PERFLUOROALKYLATION; 1,2-ALKYLARYLATION; ACRYLAMIDES; REAGENT;
D O I：
10.1016/j.tet.2015.09.004
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel and mild fluorination/cyclization reaction of activated alkenes under metal-free conditions has been developed. Fluorinated radicals were produced from halogenated hydrocarbons by simple rongalit, meanwhile, no metal and extra base are needed. This method provides a general and rapid route to construct fluorinated 2-oxindoles in aqueous solution. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：8416 / 8423
页数：8
相关论文
共 50 条
  • [11] Metal-Free Addition of Alkyl Bromides to Access 3,3-Disubstituted Quinoxalinones Enabled by Visible-Light Photoredox Catalysis
    Liao, Jennie
    Hunter, David N.
    Oloyede, Ugochinyere Nancy
    McLaughlin, Joseph W.
    Wang, Cheng
    El Marrouni, Abdellatif
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16): : 11762 - 11766
  • [12] Rhodium-Catalyzed Enantioselective Reductive Arylation: Convenient Access to 3,3-Disubstituted Oxindoles
    Jang, Young Jin
    Larin, Egor M.
    Lautens, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (39) : 11927 - 11930
  • [13] Transition-Metal-Mediated Routes to 3,3-Disubstituted Oxindoles through Anilide Cyclisation
    Klein, Johannes E. M. N.
    Taylor, Richard J. K.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (34) : 6821 - 6841
  • [14] TfOH-Catalyzed Cascade Reaction: Metal-Free Access to 3,3-Disubstituted Phthalides from o-Alkynylbenzoic Acids
    Zhang, Yanqiu
    Zhang, Zhiliang
    Xia, Yunxin
    Wang, Jiayi
    Peng, Yanqing
    Song, Gonghua
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (18): : 12924 - 12934
  • [15] Silyl Cation-Initiated, Bronsted Acid-Catalyzed Strategy toward Unsymmetrical 3,3-Disubstituted 2-Oxindoles and Azonazine Cores
    Khan, Jabir
    Yadav, Naveen
    Tyagi, Aparna
    Hazra, Chinmoy Kumar
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (16): : 11097 - 11111
  • [16] Copper-catalyzed enantioselective arylboronation of activated alkenes leading to chiral 3,3′-disubstituted oxindoles
    Chen, Jiangfei
    Li, Jin-Heng
    Zhu, Yan-Ping
    Wang, Qiu-An
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (11) : 2532 - 2536
  • [17] Metal-Free Radical Azidoarylation of Alkenes: Rapid Access to Oxindoles by Cascade CN and CC Bond-Forming Reactions
    Matcha, Kiran
    Narayan, Rishikesh
    Antonchick, Andrey P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) : 7985 - 7989
  • [18] Palladium-Catalyzed Aryl-Furanylation of Alkenes: Synthesis of Benzofuran-Containing 3,3-Disubstituted Oxindoles
    Qi, Hongbo
    Han, Kaiming
    Chen, Shufeng
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (14): : 9384 - 9395
  • [19] Metal-Free Regioselective Hydrophosphorodithioation of Spirovinylcyclopropyl Oxindoles: Rapid Access to Allyl Dialkylphosphorodithioates
    Wang, Jiahua
    Han, Fang
    Hao, Siyuan
    Tang, Yu-Jiang
    Xiong, Cheng
    Xiong, Lin
    Li, Xiancheng
    Lu, Jinrong
    Zhou, Qingfa
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (19): : 12844 - 12853
  • [20] PyBroP-mediated nucleophilic addition of oxindoles with pyridine N-oxides to access 3-pyridyl-3,3-disubstituted oxindoles
    Han, Fuzhong
    Xiao, Wenjia
    Jia, Lina
    Hu, Xiangping
    NEW JOURNAL OF CHEMISTRY, 2024, 48 (03) : 1192 - 1199
12345