On the Lewis base-promoted alkynylation of electron-deficient fluorobenzenes with trimethylsilylacetylenes

被引:4
|
作者
Sanji, Takanobu [1 ]
Watanabe, Satoru
Iyoda, Tomokazu
机构
[1] Japan Sci & Technol Agcy JST, Exploratory Res Adv Technol ERATO, Iyoda Supra Integrated Mat Project iSIM, Midori Ku, 4259-S2-3 Nagatsuta, Yokohama, Kanagawa 2268503, Japan
关键词
SNAr; Lewis base; Alkynylation; Fluorobenzene; NUCLEOPHILIC AROMATIC-SUBSTITUTION; ARYL; REACTIVITY; ALDEHYDES; CHEMISTRY; FLUORINE; REAGENTS; ALKYNES;
D O I
10.1016/j.tetlet.2016.03.068
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Lewis base-promoted alkynylation of fluorobenzenes using trimethylsilylacetylenes studying the reactivity as a function of the number of fluoride groups is described. The reaction of 1-(pentafluorophenyl)- and 1-(3,4,5-trifluorophenyl)-2-phenylacetylenes and 1-(4-methoxypheny1)-2-trimethylsilylacetylene with CsF/18-crown-6 in DMSO gave the alkynylated products in moderate to good yields with high regioselectivity under mild conditions. However, the 3,4-difluorophenyl derivative showed low reactivity. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1921 / 1924
页数:4
相关论文
共 50 条
  • [31] REDUCTIVE COUPLING OF KETONES OR ALDEHYDES WITH ELECTRON-DEFICIENT ALKENES PROMOTED BY SAMARIUM DIIODIDE
    FUKUZAWA, S
    NAKANISHI, A
    FUJINAMI, T
    SAKAI, S
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (08) : 624 - 625
  • [32] Chalcogenide-Lewis acid mediated reactions of electron-deficient alkynes with aldehydes
    Kinoshita, S
    Kinoshita, H
    Iwamura, T
    Watanabe, S
    Kataoka, T
    CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (07) : 1496 - 1502
  • [33] Visible light-promoted alkylation of electron-deficient alkenes with alkylsilyl peroxides
    Nagano, Shuji
    Maeda, Natsumi
    Kato, Terumasa
    Matsumoto, Akira
    Maruoka, Keiji
    TETRAHEDRON LETTERS, 2023, 122
  • [34] OXYGEN PROMOTED ADDITION OF 1,3-DIOXOLANE TO ELECTRON-DEFICIENT ALKENES
    WATANABE, Y
    TSUJI, Y
    TAKEUCHI, R
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (05) : 1428 - 1430
  • [35] HYDROTALCITE-PROMOTED EPOXIDATION OF ELECTRON-DEFICIENT ALKENES WITH HYDROGEN-PEROXIDE
    CATIVIELA, C
    FIGUERAS, F
    FRAILE, JM
    GARCIA, JI
    MAYORAL, JA
    TETRAHEDRON LETTERS, 1995, 36 (23) : 4125 - 4128
  • [36] Base-catalyzed stereospecific isomerization of electron-deficient allylic halides
    Erro, Samuel Martinez
    Garcia-Vazquez, Victor
    Sanz-Marco, Amparo
    Martin-Matute, Belen
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [37] Recent Advances in Lewis Base-Catalysed Chemo-, Diastereo- and Enantiodivergent Reactions of Electron-deficient Olefins and Alkynes
    Meng, Yinggao
    Chen, Lihui
    Li, Er-Qing
    CHEMICAL RECORD, 2022, 22 (04):
  • [38] Morita-Baylis-Hillman adduct derivatives (MBHADs): versatile reactivity in Lewis base-promoted annulation
    Xie, Peizhong
    Huang, You
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (32) : 8578 - 8595
  • [39] Computational Evidence for Lewis Base-Promoted CO2 Hydrogenation to Formic Acid on Gold Surfaces
    Lv, Xiangying
    Lu, Gang
    Wang, Zhi-Qiao
    Xu, Zhong-Ning
    Guo, Guo-Cong
    ACS CATALYSIS, 2017, 7 (07): : 4519 - 4526
  • [40] Dearomatization and reactivity of benzene and electron-deficient arenes promoted by π-basic transition metal complexes
    Smith, Jacob
    Myers, Jeffery
    Wilson, Katy
    Harman, Walter
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255