N-heterocyclic carbenes. IV.1synthesis of symmetrical and unsymmetrical imidazolium salts with abietane moiety

被引：9
|
作者：
Glushkov, V. A. [1 ,3 ]
Arapov, K. A. [1 ]
Kotelev, M. S. [1 ]
Rudowsky, K. S. [1 ]
Suponitsky, K. Yu [2 ]
Gorbunov, A. A. [3 ]
Maiorova, O. A. [3 ]
Slepukhin, P. A. [4 ]
机构：
[1] Perm State Univ, Fac Chem, Perm 614990, Russia
[2] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia
[3] Russian Acad Sci, Urals Branch, Inst Tech Chem, Perm 614013, Russia
[4] Russian Acad Sci, Urals Branch, I Ya Postovsky Inst Organ Synth, Ekaterinburg 620041, Russia
来源：
HETEROATOM CHEMISTRY | 2012年 / 23卷 / 01期
关键词：
OLEFIN-METATHESIS CATALYSTS; CROSS-COUPLING REACTIONS; MODULAR SYNTHESIS; IONIC LIQUIDS; METAL-COMPLEXES; LIGANDS; ARYL; NHC; PRECATALYST; BEARING;
D O I：
10.1002/hc.20745
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Methyl 12-chloromethyl-dehydroabie-tate reacts with 1-benzyl- and 1-arylimidazoles to give unsymmetrically substituted imidazolium chlorides (1ai), with abietane moiety. Starting from methyl 12-aminodehydroabietate, symmetrically substituted diterpene-based salts of imidazolinium (4) and imidazolium (5) were synthesized. Anion exchange afforded corresponding (1e center dot BF4) and (1e center dot PF6). The new compounds were tested as ligands for a Pd-catalyzed Suzuki-Miyaura reaction. The molecular structure of (1e) is reported. (C) 2011 Wiley Periodicals, Inc. Heteroatom Chem 23:515, 2012; View this article online at . DOI 10.1002/hc.20745
引用
收藏
页码：5 / 15
页数：11
相关论文
共 50 条
  • [1] Selective Activation of Fluoroalkenes with N-Heterocyclic Carbenes: Synthesis of N-Heterocyclic Fluoroalkenes and Polyfluoroalkenyl Imidazolium Salts
    Leclerc, Matthew C.
    Gorelsky, Serge I.
    Gabidullin, Bulat M.
    Korobkov, Ilia
    Baker, R. Tom
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (24) : 8063 - 8067
  • [2] N-Heterocyclic Carbenes: V. Synthesis of imidazolium salts from lupane series
    Glushkov, V. A.
    Zhiguleva, M. A.
    Maiorova, O. A.
    Gorbunov, A. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (05) : 699 - 704
  • [3] N-Heterocyclic Carbenes: V. Synthesis of imidazolium salts from lupane series
    V. A. Glushkov
    M. A. Zhiguleva
    O. A. Maiorova
    A. A. Gorbunov
    Russian Journal of Organic Chemistry, 2012, 48 : 699 - 704
  • [4] N-heterocyclic carbenes: VII. Abietane-based adamantylimidazolium salts
    Gorbunov, A. A.
    Denisov, M. S.
    Karmanov, V. I.
    Glushkov, V. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (07) : 1062 - 1066
  • [5] N-heterocyclic carbenes: VII. Abietane-based adamantylimidazolium salts
    A. A. Gorbunov
    M. S. Denisov
    V. I. Karmanov
    V. A. Glushkov
    Russian Journal of Organic Chemistry, 2013, 49 : 1062 - 1066
  • [6] Thiazole-annelated imidazolium salts:: A new architecture for N-heterocyclic carbenes
    Lohre, Claudia
    Froehlich, Roland
    Glorius, Frank
    SYNTHESIS-STUTTGART, 2008, (14): : 2221 - 2228
  • [7] Routes toward the synthesis of symmetrical triazole N-heterocyclic carbenes
    Haugen, Bryan
    Guino-o, Marites A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [8] Unsymmetrical N-heterocyclic carbenes with a 1,1′-ferrocenediyl backbone
    Rittinghaus, Stefan
    Faerber, Christian
    Bruhn, Clemens
    Siemeling, Ulrich
    DALTON TRANSACTIONS, 2014, 43 (09) : 3508 - 3520
  • [9] N-Heterocyclic carbenes: VI. Abietane-based chiral benzimidazolium salts as N-heterocyclic carbene ligands in the heck reaction
    V. A. Glushkov
    E. N. Teplykh
    M. S. Denisov
    A. A. Gorbunov
    Russian Journal of Organic Chemistry, 2012, 48 : 815 - 819
  • [10] N-Heterocyclic carbenes: VI. Abietane-based chiral benzimidazolium salts as N-heterocyclic carbene ligands in the heck reaction
    Glushkov, V. A.
    Teplykh, E. N.
    Denisov, M. S.
    Gorbunov, A. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (06) : 815 - 819
12345