Addition of pyrroles onto terminal alkynes catalyzed by a dinuclear ruthenium (II) complex

被引:19
|
作者
Tan, Sze Tat [1 ]
Teo, Yew Chin [1 ]
Fan, Wai Yip [1 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
关键词
Ruthenium complexes; Pyrrole; Alkynes; Hydroarylation; H BOND ACTIVATION; POLYNUCLEAR COMPOUNDS; COUPLING REACTION; CHEMISTRY; HYDROARYLATION; REGIOSELECTIVITY; HYDROFORMYLATION; DIPYRROMETHANES; ALKALOIDS; EFFICIENT;
D O I
10.1016/j.jorganchem.2012.02.017
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The addition of pyrroles onto alkynes has been catalyzed by a dinuclear ruthenium complex, Ru2(CO)4(PPh3)2Br4, resulting in the formation of geminal 2-vinylpyrroles in high yields under mild conditions. Further functionalization with pyrroles or alkynes to afford dipyrrolmethanes or 2,5-bis(vinyl) pyrroles via the vinyl functional group can readily be achieved. A mechanism involving cationic ruthenium complexes was proposed based on the product regioselectivity, deuteration and infrared spectroscopic studies carried out on the catalytic process. (C) 2012 Elsevier B.V. All rights reserved.
引用
下载
收藏
页码:58 / 64
页数:7
相关论文
共 50 条
  • [21] Mechanism of co-dimerization of vinylboronates with terminal alkynes catalyzed by ruthenium-hydride complex
    Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, Poznań
    61-614, Poland
    不详
    61-614, Poland
    J. Mol. Catal. A Chem., (239-244):
  • [22] Alkoxide-catalyzed addition of terminal alkynes to ketones
    Babler, JH
    Liptak, VP
    Phan, N
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01): : 416 - 417
  • [23] Mechanism of co-dimerization of vinylboronates with terminal alkynes catalyzed by ruthenium-hydride complex
    Pyziak, Jadwiga
    Walkowiak, Jedrzej
    Hoffmann, Marcin
    Marciniec, Bogdan
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2015, 396 : 239 - 244
  • [24] Ruthenium Catalyzed Hydroboration of Terminal Alkynes to Z-Vinylboronates
    Gunanathan, Chidambaram
    Hoelscher, Markus
    Pan, Fangfang
    Leitner, Walter
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (35) : 14349 - 14352
  • [25] ORGN 445-Ruthenium-catalyzed addition of imides to alkynes
    Goossen, Lukas J.
    Blanchot, Mathieu
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [26] ADDITION OF CARBOXYLIC-ACIDS TO ALKYNES CATALYZED BY RUTHENIUM COMPLEXES
    ROTEM, M
    SHVO, Y
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 448 (1-2) : 189 - 204
  • [27] Platinum(II)-catalyzed addition of alcohols to alkynes
    Hartman, JW
    Sperry, L
    TETRAHEDRON LETTERS, 2004, 45 (19) : 3787 - 3788
  • [28] Iridium complex-catalyzed addition of water and alcohols to non-activated terminal alkynes
    Hirabayashi, T
    Okirnoto, Y
    Saito, A
    Morita, M
    Sakaguchi, S
    Ishii, Y
    TETRAHEDRON, 2006, 62 (10) : 2231 - 2234
  • [29] Theoretical Mechanism for Selective Catalysis of Ruthenium Complex Catalyzed Hydroboration of Terminal Alkynes to Z-Vinylboronates
    Sun, Chuanzhi
    Liu, Mingshu
    Sun, Haitao
    Hang, Fang
    Sun, Nan
    Chen, Dezhan
    INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2015, 115 (02) : 59 - 67
  • [30] Iridium-catalyzed addition of acid chlorides to terminal alkynes
    Iwai, Tomohiro
    Fujihara, Tetsuaki
    Terao, Jun
    Tsuji, Yasushi
    Journal of the American Chemical Society, 2009, 131 (19): : 6668 - 6669