AgF-Mediated Dialkylation of Activate Alkenes: An Efficient Access to Nitrile-Containing Spirooxindoles

被引:12
|
作者
Wu, Liang [1 ]
Chen, Pinhong [1 ]
Liu, Guosheng [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
关键词
spirooxindoles; activated alkenes; silver fluoride; acetonitrile; C-H bond cleavage; CATALYZED OXIDATIVE ARYLALKYLATION; ENANTIOSELECTIVE SYNTHESIS; BOND-CLEAVAGE; C-H; AMINOFLUORINATION; FLUORINATION;
D O I
10.1002/cjoc.201400350
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel Ag-mediated dialkylation reaction of alkenes was disclosed, in which AgF was essential to activate C-H bond of acetonitrile. This reaction provided an efficient way to nitrile-containing spirooxindoles from readily available (1H-indol-3-yl)methanamine derivatives.
引用
收藏
页码:681 / 684
页数:4
相关论文
共 10 条
  • [1] Regioselective Access to 2-Iminoimidazolidines via AgF-Mediated Cascade Reactions
    He, Yiting
    Wu, Haiting
    Liang, Yunshi
    Deng, Huiying
    Xiang, Lingling
    Gu, Jiangyong
    Zhang, Jing
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (11): : 7480 - 7486
  • [2] AgF-Mediated Fluorinative Cross-Coupling of Two Olefins: Facile Access to α-CF3 Alkenes and β-CF3 Ketones
    Gao, Bing
    Zhao, Yanchuan
    Hu, Jinbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (02) : 638 - 642
  • [3] Nitrile-containing copper(ii) porphyrin coordination complexes for efficient anticancer activity and mechanism research
    Zhang, Qian
    Liu, Jin-Li
    Feng, Xiao-Xia
    Liu, Jia-Cheng
    NEW JOURNAL OF CHEMISTRY, 2021, 45 (11) : 5221 - 5227
  • [4] Activated-Carbon-Supported Calcium Oxide: A Selective and Efficient Catalyst for Nitrile-Containing Diaryl Ether Synthesis
    Han, Yue
    Wang, Guangxing
    Qiu, Wenfeng
    Guo, Ying
    Sun, Yanan
    Zhang, Youlan
    Zhou, Heng
    Zhao, Tong
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (12) : 2511 - 2517
  • [5] Iron-Catalyzed Cascade Carbochloromethylation of Activated Alkenes: Highly Efficient Access to Chloro-Containing Oxindoles
    Lu, Ming-Zhu
    Loh, Teck-Peng
    ORGANIC LETTERS, 2014, 16 (18) : 4698 - 4701
  • [6] Lewis-Acid-Mediated Intramolecular Trifluoromethylthiolation of Alkenes with Phenols: Access to SCF3-Containing Chromane and Dihydrobenzofuran Compounds
    Song, Xu-Feng
    Ding, Tong-Mei
    Zhu, Deng
    Huang, Jie
    Chen, Zhi-Min
    ORGANIC LETTERS, 2020, 22 (17) : 7052 - 7056
  • [7] Nickel-Catalyzed Intramolecular Dual Annulation Reaction of Alkyl Nitrile-Containing 1,2,3-Benzotriazin-4(3H)-ones: A Pathway to Access Diversely Polycyclic Quinazolinone Alkaloids
    Thorat, Vijaykumar H.
    Huang, Yong-Ran
    Chao, Hao-Yu
    Hsieh, Jen-Chieh
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (09) : 2130 - 2135
  • [8] An efficient 1,3-dipolar cycloaddition between aromatic selenoaldehydes and nitrile oxides or nitrile imines: an easy access to selenium-containing five-membered heterocyclic ring system
    Segi, Masahito
    Tanno, Katsuhiko
    Kojima, Masurni
    Honda, Mitsunori
    Nakajima, Tadashi
    TETRAHEDRON LETTERS, 2007, 48 (13) : 2303 - 2306
  • [9] Hypervalent iodine-mediated interaction of aldoximes with activated alkenes including Baylis-Hillman adducts: a new and efficient method for the preparation of nitrile oxides from aldoximes
    Das, B
    Holla, H
    Mahender, G
    Banerjee, J
    Reddy, MR
    TETRAHEDRON LETTERS, 2004, 45 (39) : 7347 - 7350
  • [10] Highly Efficient lsobutyraldehyde-Mediated Epoxidation of Cyclic Alkenes with Dioxygen Catalyzed by a Novel Dimeric Manganese(II) Complex Containing an Easy-to-Prepare Flexible Carboxamide Ligand
    Khavasi, Hamid Reza
    Sasan, Koroush
    Pirouzmand, Mahtab
    Ebrahimi, Samad Nejad
    INORGANIC CHEMISTRY, 2009, 48 (13) : 5593 - 5595