Ruthenium(II)/N-Heterocyclic Carbene Catalyzed [3+2] Carbocyclization with Aromatic NH Ketimines and Internal Alkynes

被引：122
作者：
Zhang, Jing [1 ]
Ugrinov, Angel [1 ]
Zhao, Pinjing [1 ]
机构：
[1] N Dakota State Univ, Dept Chem & Biochem, Fargo, ND 58108 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 26期
关键词：
CH activation; indenamine; NH ketimines; N-heterocyclic carbenes; ruthenium; H BOND ACTIVATION; CARBON-HYDROGEN BONDS; C-H; ROOM-TEMPERATURE; HETEROCYCLIC CARBENES; BENZOPHENONE IMINE; ARYL CHLORIDES; RUTHENIUM; COMPLEXES; ANNULATION;
D O I：
10.1002/anie.201209031
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Convenient and highly efficient: Indenamines were synthesized using the title reaction, which occurs at ambient temperature, in the absence of oxidants or other metal salts, and in nonpolar solvents. A proposed mechanism involves imine-directed activation of an aromatic C-H bond, alkyne insertion, and carbocyclization by intramolecular imine insertion into Ru-alkenyl linkages. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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收藏
页码：6681 / 6684
页数：4
相关论文
共 67 条
  • [51] EFFICIENT CATALYTIC ADDITION OF AROMATIC CARBON-HYDROGEN BONDS TO OLEFINS
    MURAI, S
    KAKIUCHI, F
    SEKINE, S
    TANAKA, Y
    KAMATANI, A
    SONODA, M
    CHATANI, N
    [J]. NATURE, 1993, 366 (6455) : 529 - 531
  • [52] Muralirajan K., 2011, ANGEW CHEM, V123, P4255
  • [53] Nolan S P., 2006, N HETEROCYCLIC CARBE
  • [54] Diverse Strategies toward Indenol and Fulvene Derivatives: Rh-Catalyzed C-H Activation of Aryl Ketones Followed by Coupling with Internal Alkynes
    Patureau, Frederic W.
    Besset, Tatiana
    Kuhl, Nadine
    Glorius, Frank
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) : 2154 - 2156
  • [55] Rh(III)-Catalyzed Directed C-H Olefination Using an Oxidizing Directing Group: Mild, Efficient, and Versatile
    Rakshit, Souvik
    Grohmann, Christoph
    Besset, Tatiana
    Glorius, Frank
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (08) : 2350 - 2353
  • [56] C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation
    Song, Guoyong
    Wang, Fen
    Li, Xingwei
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3651 - 3678
  • [57] Rhodium(III)-Catalyzed Arene and Alkene C-H Bond Functionalization Leading to Indoles and Pyrroles
    Stuart, David R.
    Alsabeh, Pamela
    Kuhn, Michelle
    Fagnou, Keith
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (51) : 18326 - 18339
  • [58] Direct C-H Transformation via Iron Catalysis
    Sun, Chang-Liang
    Li, Bi-Jie
    Shi, Zhang-Jie
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1293 - 1314
  • [59] Tertiary Carbinamine Synthesis by Rhodium-Catalyzed [3+2] Annulation of N-Unsubstituted Aromatic Ketimines and Alkynes
    Sun, Zhong-Ming
    Chen, Shuo-Ping
    Zhao, Pinjing
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (08) : 2619 - 2627
  • [60] Tran D. N., 2011, ANGEW CHEM, V123, P11294
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