A convenient synthesis of quinolizinium salts through Rh(III) or Ru(II)-catalyzed C-H bond activation of 2-alkenylpyridines

被引:71
作者
Luo, Ching-Zong [1 ]
Gandeepan, Parthasarathy [1 ]
Cheng, Chien-Hong [1 ]
机构
[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan
关键词
WESTPHAL CONDENSATION; DERIVATIVES; ALKYNES; ROUTE; SEMPERVIRINE; OLEFINATION; ANALOGS; RH;
D O I
10.1039/c3cc45004j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient synthesis of quinolizinium salts from 2-vinylpyridines and alkynes via Rh(III) or Ru(II)-catalyzed C-H activation and annulation reaction is described. A possible mechanism involving pyridine assisted vinylic ortho-C-H activation, alkyne insertion and reductive elimination is proposed.
引用
收藏
页码:8528 / 8530
页数:3
相关论文
共 50 条
  • [41] Rh(iii)-catalyzed synthesis of tetracyclic isoquinolinium salts via C-H activation and [4+2] annulation of 1-phenyl-3,4-dihydroisoquinolines and alkynes in ethanol
    Dang, Xinxin
    He, Yu
    Liu, Yingtian
    Chen, Xuehong
    Li, Jun-Long
    Zhou, Xian-Li
    Jiang, Hezhong
    Li, Jiahong
    RSC ADVANCES, 2018, 8 (52): : 30050 - 30054
  • [42] Rh(III)-Catalyzed Oxidative Coupling of Unactivated Alkenes via C-H Activation
    Tsai, Andy S.
    Brasse, Mikael
    Bergman, Robert G.
    Ellman, Jonathan A.
    ORGANIC LETTERS, 2011, 13 (03) : 540 - 542
  • [43] Rh(III)-catalyzed C-H activation/cyclization of benzamides and diazo compounds to form isocoumarins and α-pyrones
    Li, Xing Guang
    Sun, Min
    Liu, Kai
    Jin, Qiao
    Liu, Pei Nian
    CHEMICAL COMMUNICATIONS, 2015, 51 (12) : 2380 - 2383
  • [44] On the selectivity in some Rh(III) catalyzed C-H activation cross-couplings
    Patureau, Frederic William
    Besset, Tatiana
    Froehlich, Roland
    Glorius, Frank
    COMPTES RENDUS CHIMIE, 2012, 15 (11-12) : 1081 - 1085
  • [45] Synthesis of Mesoionic Isoquinolines by Rhodium(III)-Catalyzed C-H Activation
    Zhang, Wei
    Wang, Cheng-Qi
    Lin, Hui
    Dong, Lin
    Xu, Yan-Jun
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (03) : 907 - 910
  • [46] Rh(III)-Catalyzed Regioselective Acetylation of sp2 C-H Bond Starting from Paraformaldehyde
    Wan, Ting
    Du, Sidong
    Pi, Chao
    Wang, Yong
    Li, Rongbin
    Wu, Yangjie
    Cui, Xiuling
    CHEMCATCHEM, 2019, 11 (16) : 3791 - 3796
  • [47] Rhodium(III)-Catalyzed Redox-Neutral Synthesis of Isoquinolinium Salts via C-H Activation of Imines
    Tian, Miaomiao
    Zheng, Guangfan
    Fan, Xuesen
    Li, Xingwei
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (12) : 6477 - 6488
  • [48] Intermolecular Amination of Ketoximes with Anthranils by Rh-Catalyzed C-H Bond Activation in Air
    Chen, Weiqiang
    Li, Chao-Yi
    Li, Hui-Jing
    Wu, Yan-Chao
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (04) : 838 - 844
  • [49] C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation
    Song, Guoyong
    Wang, Fen
    Li, Xingwei
    CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3651 - 3678
  • [50] Synthesis of Ferrocene-Based Pyridinones through Rh(III)-Catalyzed Direct C-H Functionalization Reaction
    Wang, Shao-Bo
    Zheng, Jun
    You, Shu-Li
    ORGANOMETALLICS, 2016, 35 (10) : 1420 - 1425