B(C6F5)3-mediated direct intramolecular C7-alkenylation of N-propargylindoles

被引:2
|
作者
Cui, Jie [1 ]
Wang, Tongdao [1 ]
机构
[1] Dalian Univ Technol, Sch Chem, Dalian 116024, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H; INDOLE ALKALOIDS; C7-FUNCTIONALIZATION; FUNCTIONALIZATION; REARRANGEMENT; ALKYLATION; ACTIVATION; REACTIVITY; ARYLATION; AMINES;
D O I
10.1039/d3cc02599c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
B(C6F5)(3)-mediated direct C7-alkenylation of N-propargylindoles without directing groups was developed. This reaction proceeds via the & pi;-activation of the alkynyl group with B(C6F5)(3)/Friedel-Crafts alkenylation/proton transfer reaction sequence. Interestingly, C7-alkenylation products could further convert into the fused indoles by deprotonation and finally polyaromatic N-heterocycles by the hydride abstraction.
引用
收藏
页码:10279 / 10282
页数:4
相关论文
共 50 条
  • [21] Synthesis and reactivity of [N(C6H4Br)3][B(C6F5)4]:: the X-ray crystal structure of [Fe(C5H5)2][B(C6F5)4]
    O'Connor, AR
    Nataro, C
    Golen, JA
    Rheingold, AL
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (14) : 2411 - 2414
  • [22] Triple para-substitution reactions of B(C6F5)3 and [(C6F5)3PF]+ with P(SiMe3)3
    Thomson, Jordan
    Michailovich, Sofia
    Miao, Linkun
    Farrell, Jeffrey M.
    Murray, Jillian A.
    Lough, Alan
    Stephan, Douglas W.
    DALTON TRANSACTIONS, 2024, 53 (13) : 5775 - 5778
  • [23] Cyclopropanation/Carboboration Reactions of Enynes with B(C6F5)3
    Hansmann, Max M.
    Melen, Rebecca L.
    Rudolph, Matthias
    Rominger, Frank
    Wadepohl, Hubert
    Stephan, Douglas W.
    Hashmi, A. Stephen K.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (49) : 15469 - 15477
  • [24] Reductive Deamination with Hydrosilanes Catalyzed by B(C6F5)3
    Fang, Huaquan
    Oestreich, Martin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (28) : 11394 - 11398
  • [25] Interaction of Metal Oxido Compounds with B(C6F5)3
    Zwettler, Niklas
    Moesch-Zanetti, Nadia C.
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (24) : 6064 - 6076
  • [26] B(C6F5)3-Catalyzed Hydrosilylation of Vinylcyclopropanes
    Long, Peng-Wei
    He, Tao
    Oestreich, Martin
    ORGANIC LETTERS, 2020, 22 (18) : 7383 - 7386
  • [27] Thermal Decomposition of B(C6F5)3•Py Complex
    Shcherbina, N. A.
    Kazakov, I. V.
    Gugin, N. Yu.
    Lisovenko, A. S.
    Pomogaeva, A. V.
    Kondrat'ev, Yu. V.
    Suslonov, V. V.
    Timoshkin, A. Yu.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2019, 89 (06) : 1162 - 1168
  • [28] Thermal Decomposition of B(C6F5)3·Py Complex
    N. A. Shcherbina
    I. V. Kazakov
    N. Yu. Gugin
    A. S. Lisovenko
    A. V. Pomogaeva
    Yu. V. Kondrat’ev
    V. V. Suslonov
    A. Yu. Timoshkin
    Russian Journal of General Chemistry, 2019, 89 : 1162 - 1168
  • [29] Reactions of transition-metal oxo complexes with B(C6F5)3: crystal structures of [V{OB(C6F5)3}(acac)2], [Ti{OB(C6F5)3}(acac)2] and cis-[MoO{OB(C6F5)3}(acac)2] (acac = acetylacetonate)
    Galsworthy, J. R.
    Green, M. L. H.
    Mueller, M.
    Prout, K.
    Journal of the Chemical Society.Dalton Transactions, (08):
  • [30] Crystal structure of the strongly hydrogen bonded complex anion [(C6F5)3B(H3O2)B(C6F5)3]-
    Drewitt, MJ
    Niedermann, M
    Baird, MC
    INORGANICA CHIMICA ACTA, 2002, 340 : 207 - 210