SYNTHESIS OF 3-ARYL-1,2-DICARBA-CLOSO-DODECABORANES BY SUZUKI-MIYAURA COUPLING REACTION

被引:25
|
作者
Aizawa, Koei [1 ]
Ohta, Kiminori [1 ]
Endo, Yasuyuki [1 ]
机构
[1] Tohoku Pharmaceut Univ, Fac Pharmaceut Sci, Aoba Ku, Sendai, Miyagi 9818558, Japan
关键词
Suzuki-Miyaura Coupling Reaction; Carborane; 3-lodo-o-carborane; 3-Aryl-o-carborane; Boronic Acid; DERIVATIVES; CARBORANES; CHEMISTRY; REAGENTS; ESTERS;
D O I
10.3987/COM-09-S(S)32
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In contrast to conventional syntheses of 3-aryl-o-carborane derivatives, which involve reconstruction of the o-carborane cage or Pd-catalyzed coupling reaction of 3-iodo-o-carborane with Grignard reagents, the Suzuzki-Miyaura coupling reaction of 3-iodo-o-carborane proceeds with a variety of aryl boronic acids, providing a new route to 3-aryl-o-carborane derivatives bearing easily transformable functional groups, including CH3O-, NO2-, CHO- and CN-. This approach provides easy access to a variety of compounds with a 3-aryl-o-carborane scaffold.
引用
收藏
页码:369 / 377
页数:9
相关论文
共 50 条
  • [1] SYNTHESIS OF 3-BENZYLOXY-1,2-DICARBA-CLOSO-DODECABORANES(12) AND 4-BENZYLOXY-1,2-DICARBA-CLOSO-DODECABORANES(12) FROM DICARBADODECABORATES(14) DIANIONS AND AROMATIC-ALDEHYDES
    ZAKHARKIN, LI
    KALININ, VN
    KOBELKOVA, NI
    SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1976, 6 (01): : 65 - 74
  • [2] New Approach to the Synthesis of 3-Alkyl-1,2-dicarba-closo-dodecaboranes: Reaction of Alkyldichloroboranes with Thallium Dicarbollide
    Safronov, Alexander V.
    Shlyakhtina, Natalia I.
    Hawthorne, M. Frederick
    ORGANOMETALLICS, 2012, 31 (07) : 2764 - 2769
  • [3] Syntheses and reductions of C-dimesitylboryl-1,2-dicarba-closo-dodecaboranes
    Kahlert, Jan
    Boehling, Lena
    Brockhinke, Andreas
    Stammler, Hans-Georg
    Neumann, Beate
    Rendina, Louis M.
    Low, Paul J.
    Weber, Lothar
    Fox, Mark A.
    DALTON TRANSACTIONS, 2015, 44 (21) : 9766 - 9781
  • [4] Synthesis, Molecular Structure, and Electrochemistry of 1-Ferrocenyl-1,2-dicarba-closo-dodecaboranes
    Korotvicka, Ales
    Snajdr, Ivan
    Stepnicka, Petr
    Cisarova, Ivana
    Janousek, Zbynek
    Kotora, Martin
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2013, (15) : 2789 - 2798
  • [5] CHEMISTRY OF BORANES .27. LEWIS ACIDITY OF SOME SUBSTITUTED 1,2-DICARBA-CLOSO-DODECABORANES
    PLESEK, J
    HERMANEK, S
    HANOUSEK, F
    HANSLIK, T
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1972, 37 (10) : 3403 - &
  • [6] Acidic hydrolysis of N-acyl-1-substituted 3-amino-1,2-dicarba-closo-dodecaboranes
    Levit, GL
    Demin, AM
    Kodess, MI
    Ezhikova, MA
    Sadretdinova, LS
    Ol'shevskaya, VA
    Kalinin, VN
    Krasnov, VP
    Charushin, VN
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (11) : 2783 - 2786
  • [7] SYNTHESIS OF 9-ORGANYL-1,2-DICARBA-CLOSO-DODECABORANES(12) AND 9-ORGANYL-1,7-DICARBA-CLOSO-DODECABORANES(12) VIA THE CROSS-COUPLING REACTIONS BETWEEN ORGANOZINC COMPOUNDS AND 9-IODO-1,2-DICARBA-CLOSO-DODECABORANE OR 9-IODO-1,7-DICARBA-CLOSO-DODECABORANE
    ZAKHARKIN, LI
    OLSHEVSKAYA, VA
    SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1991, 21 (6-7): : 1041 - 1046
  • [8] New synthetic method of 1,2-diaryl-1,2-dicarba-closo-dodecaboranes employing aromatic nucleophilic substitution (SNAr) reaction
    Ohta, K
    Goto, T
    Endo, Y
    TETRAHEDRON LETTERS, 2005, 46 (03) : 483 - 485
  • [9] Approaches to trinuclear half-sandwich carbene complexes containing 1,2-dicarba-closo-dodecaboranes
    Xiao, Xu-Qiong
    Lin, Yue-Jian
    Jin, Guo-Xin
    DALTON TRANSACTIONS, 2008, 19 (19) : 2615 - 2619
  • [10] NMR study of 1-aryl-1,2-dicarba-closo-dodecaboranes:: intramolecular C-H•••O hydrogen bonding in solution
    Ohta, K
    Yamazaki, H
    Endo, Y
    TETRAHEDRON LETTERS, 2006, 47 (12) : 1937 - 1940