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
来源：
CHEMICAL COMMUNICATIONS | 2013年 / 49卷 / 76期
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
  • [21] Rh(<sc>iii</sc>)-catalyzed aldehydic and aryl C-H alkylation with cyclopropanols via C-H/C-C bond activation
    Dash, Om Prakash
    Garg, Divya
    Volla, Chandra M. R.
    CHEMICAL COMMUNICATIONS, 2024, 60 (76) : 10576 - 10579
  • [22] Rh(III)-Catalyzed Enaminone-Directed Alkenyl C-H Activation for the Synthesis of Salicylaldehydes
    Qi, Bing
    Guo, Shan
    Zhang, Wenjing
    Yu, Xiaolong
    Song, Chao
    Zhu, Jin
    ORGANIC LETTERS, 2018, 20 (13) : 3996 - 3999
  • [23] Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation
    Kumar, Sanjeev
    Nunewar, Saiprasad
    Usama, Khan Mohammad
    Kanchupalli, Vinaykumar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (15) : 2223 - 2229
  • [24] Rh(III)-Catalyzed C-H Activation/Cyclization of Indoles and Pyrroles: Divergent Synthesis of Heterocycles
    Zhang, Yan
    Zheng, Jing
    Cui, Sunliang
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (14) : 6490 - 6500
  • [25] Rh(III)-Catalyzed Oxidative Annulation of 2-Arylquinoxalines with Cyclic 2-Diazo-1,3-diketones by C-H Bond Activation
    Ajay, Chidrawar
    Chary, Devulapally Yogananda
    Balasubramanian, Sridhar
    Reddy, Basi Subba V.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (13)
  • [26] Direct Synthesis of Protoberberine Alkaloids by Rh-Catalyzed C-H Bond Activation as the Key Step
    Jayakumar, Jayachandran
    Cheng, Chien-Hong
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (05) : 1800 - 1804
  • [27] Ligand design for Rh(III)-catalyzed C-H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones
    Hyster, Todd K.
    Dalton, Derek M.
    Rovis, Tomislav
    CHEMICAL SCIENCE, 2015, 6 (01) : 254 - 258
  • [28] Recent Advances in the Synthesis of Quaternary Ammonium Salts via Transition-Metal-Catalyzed C-H Bond Activation
    Jayakumar, Jayachandran
    Cheng, Chien-Hong
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2018, 65 (01) : 11 - 23
  • [29] Rh(III)-Catalyzed Oxidative C-H Activation/Annulation of Salicylaldehydes with Masked Enynes for the Synthesis of Chromones
    Li, Bo
    Zhu, Jianping
    Zheng, Xia
    Ti, Wenqing
    Huang, Yue
    Yao, Hequan
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (01) : 548 - 558
  • [30] Rh(III)-catalyzed aromatic C-H bond carbenoid functionalization of triazenes by α-diazomalonate
    Wang, Dahai
    Cui, Sunliang
    TETRAHEDRON, 2016, 72 (22) : 2725 - 2730
12345