Isoquinoline Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling/Cyclization of Aryl Aldimines and Alkynes

被引：410
|
作者：
Guimond, Nicolas [1 ]
Fagnou, Keith [1 ]
机构：
[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 34期
基金：
加拿大自然科学与工程研究理事会;
关键词：
C-H ACTIVATION; POMERANZ-FRITSCH REACTION; INTERNAL ALKYNES; ELECTROPHILIC CYCLIZATION; TERMINAL ACETYLENES; PYRIDINES; IMINES; IMINOANNULATION; DERIVATIVES; CLEAVAGE;
D O I：
10.1021/ja904380q
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A general. rhodium-catalyzed oxidative coupling reaction between internal alkynes and aryl aldimines is described. This process affords 3,4-disubstituted isoquinolines in good yield and high regioselectivity. Preliminary mechanistic studies suggest that the C-N bond formation arises from the reductive elimination of a rhodium(III) species.
引用
收藏
页码：12050 / +
页数：4
相关论文
共 50 条
  • [1] Isoquinoline synthesis via rhodium-catalyzed oxidative cross-coupling/ cyclization of aryl aldimines and alkynes
    Guimond, Nicolas
    Fagnou, Keith
    Journal of the American Chemical Society, 2009, 131 (34): : 12050 - 12051
  • [2] Rhodium-catalyzed triarylphosphine synthesis via cross-coupling of aryl iodides and acylphosphines
    Yang, Jiefang
    Wu, Hongyu
    Wang, Zhiqian
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2018, 22 (01) : 1 - 5
  • [3] Rhodium-catalyzed direct oxidative cross-coupling of 2-aryl pyridine with benzothiazoles
    Liu, Hui
    Xu, Huan
    Yuan, Yu
    TETRAHEDRON, 2014, 70 (37) : 6474 - 6481
  • [4] Rhodium-catalyzed cross-coupling of aryl carbamates with arylboron reagents
    Nakamura, Keisuke
    Yasui, Kosuke
    Tobisu, Mamoru
    Chatani, Naoto
    TETRAHEDRON, 2015, 71 (26-27) : 4484 - 4489
  • [5] Rhodium-catalyzed selective cross-coupling of internal alkynes with a terminal silylacetylene
    Katagiri, Takashi
    Tsurugi, Hayato
    Funayama, Atsushi
    Satoh, Tetsuya
    Miura, Masahiro
    CHEMISTRY LETTERS, 2007, 36 (07) : 830 - 831
  • [6] Rhodium-catalyzed Oxidative Coupling of Benzylamines with Alkynes through Dehydrogenation and Dehydrogenative Cyclization
    Morimoto, Keisuke
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    CHEMISTRY LETTERS, 2011, 40 (06) : 600 - 602
  • [7] RHODIUM-CATALYZED CROSS-COUPLING OF UNACTIVATED ALLENES AND 1-ALKYNES
    YAMAGUCHI, M
    OMATA, K
    HIRAMA, M
    TETRAHEDRON LETTERS, 1994, 35 (31) : 5689 - 5692
  • [8] Rhodium-Catalyzed Oxidative Coupling of Aryl Hydrazones with Internal Alkynes: Efficient Synthesis of Multisubstituted Isoquinolines
    Liu, Wenting
    Hong, Xiaohu
    Xu, Bin
    SYNTHESIS-STUTTGART, 2013, 45 (15): : 2137 - 2149
  • [9] Synthesis of Siloles via Rhodium-Catalyzed Cyclization of Alkynes and Diynes with Hexamethyldisilane
    Matsuda, Takanori
    Suda, Yuya
    Fujisaki, Yosuke
    SYNLETT, 2011, (06) : 813 - 816
  • [10] Rhodium-catalyzed Oxidative Coupling/Cyclization of Benzamides with Alkynes via C-H Bond Cleavage
    Mochida, Satoshi
    Umeda, Nobuyoshi
    Hirano, Koji
    Satoh, Tetsuya
    Miura, Masahiro
    CHEMISTRY LETTERS, 2010, 39 (07) : 744 - 746
12345