Ruthenium-catalyzed carbon-carbon bond formation via the cleavage of an unreactive aryl carbon-nitrogen bond in aniline derivatives with organoboronates

被引：170
|
作者：
Ueno, Satoshi
Chatani, Naoto
Kakiuchi, Fumitoshi
机构：
[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Kanagawa 2238522, Japan
[2] Osaka Univ, Fac Engn, Dept Appl Chem, Osaka 5650871, Japan
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 19期
关键词：
D O I：
10.1021/ja0713431
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The RuH2(CO)(PPh3)(3)-catalyzed reaction of 2-amino-6-methylacetophenone with phenylboronic acid 2,2-dimethyl-1,3-propanediol ester in refluxing toluene gave the corresponding phenylation product in 83% yield via aryl carbon-nitrogen bond cleavage. This reaction involves two notable features: (1) the coupling proceeds via the oxidative addition of an aryl carbon-nitrogen bond in anilines to the ruthenium complex, and (2) C-C bond formation takes place via transmetalation between the Ru-NR2 species and organoboronates.
引用
收藏
页码：6098 / +
页数：3
相关论文
共 50 条
  • [1] Ruthenium-catalyzed transformation of aryl and alkynyl propargyl ethers into aryl and alkynyl ketones via cleavage of a carbon-carbon triple bond
    Shen, HC
    Su, HL
    Hsueh, YC
    Liu, RS
    ORGANOMETALLICS, 2004, 23 (18) : 4332 - 4334
  • [2] Ruthenium-catalyzed β-allyl elimination leading to selective cleavage of a carbon-carbon bond in homoallyl alcohols
    Kondo, T
    Kodoi, K
    Nishinaga, E
    Okada, T
    Morisaki, Y
    Watanabe, Y
    Mitsudo, T
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (22) : 5587 - 5588
  • [3] Transition-Metal-Catalyzed Carbon-Carbon Bond Formation via Carbon-Hydrogen Bond Cleavage
    Kakiuchi, Fumitoshi
    Kochi, Takuya
    SYNTHESIS-STUTTGART, 2008, (19): : 3013 - 3039
  • [4] Ruthenium mediated carbon-carbon and carbon-nitrogen bond formation: parameters governing the reactivity of the metal centre
    Pfeffer, M
    Sutter, JP
    Urriolabeitia, EP
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1997, 134 (10-11): : 947 - 954
  • [5] CARBON-CARBON AND CARBON-NITROGEN BOND FORMATION MEDIATED BY RUTHENIUM(II) COMPLEXES - SYNTHESIS OF (1H)-ISOQUINOLINIUM DERIVATIVES
    ABBENHUIS, HCL
    PFEFFER, M
    SUTTER, JP
    DECIAN, A
    FISCHER, J
    JI, HL
    NELSON, JH
    ORGANOMETALLICS, 1993, 12 (11) : 4464 - 4472
  • [6] Ruthenium-catalyzed novel carbon-carbon bond forming reactions via ruthenium-allenylidene complexes
    Nishibayashi, Y
    Uemura, S
    CURRENT ORGANIC CHEMISTRY, 2006, 10 (02) : 135 - 150
  • [7] Alkylative amination of aldehydes via carbon-carbon bond formation based on radical addition to carbon-nitrogen double bond
    Miyabe, H
    Yamakawa, K
    Yoshioka, N
    Naito, T
    TETRAHEDRON, 1999, 55 (37) : 11209 - 11218
  • [8] A new ruthenium-catalyzed cleavage of a carbon-carbon triple bond: Efficient transformation of ethynyl alcohol into alkene and carbon monoxide
    Datta, S
    Chang, CL
    Yeh, KL
    Liu, RS
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) : 9294 - 9295
  • [9] Ruthenium-catalyzed carbon-carbon bond formation between propargylic alcohols and alkenes via the allenylidene-ene reaction
    Hidai, M. (uemura@scl.kyoto-u.ac.jp), 1600, American Chemical Society (125):
  • [10] Ruthenium-catalyzed carbon-carbon bond formation between propargylic alcohols and alkenes via the allenylidene-ene reaction
    Nishibayashi, Y
    Inada, Y
    Hidai, M
    Uemura, S
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) : 6060 - 6061
12345