Rhodium-catalyzed intramolecular [4+2] cycloadditions of alkynyl halides

被引：43
|
作者：
Yoo, WJ [1 ]
Allen, A [1 ]
Villeneuve, K [1 ]
Tam, W [1 ]
机构：
[1] Univ Guelph, Guelph Waterloo Ctr Grad Work Chem & Biochem, Dept Chem, Guelph, ON N1G 2W1, Canada
来源：
ORGANIC LETTERS | 2005年 / 7卷 / 26期
关键词：
D O I：
10.1021/ol052412o
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] Cationic rhodium(l)-catalyzed intramolecular [4 + 2] cycloadditions of diene-tethered alkynyl halides were found to occur in good yields (70-87%). The halide moiety is compatible with the cycloaddition reactions, and no oxidative insertion to the alkynyl halide was observed. The halogen-containing cycloadducts could be transformed into a variety of products that are difficult or impossible to obtain via direct cycloaddition.
引用
收藏
页码：5853 / 5856
页数：4
相关论文
共 50 条
  • [1] Rhodium-catalyzed intramolecular [4+2] cycloadditions of alkynyl halides
    Yoo, Woo-Jin
    Allen, Anna
    Villeneuve, Karine
    Tam, William
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [2] Iridium-catalyzed intramolecular [4+2] cycloadditions of alkynyl halides
    Tigchelaar, Andrew
    Tam, William
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1765 - 1770
  • [3] Rhodium-Catalyzed Enantioselective [4+2] Cycloadditions of Vinylcarbenes with Dienes
    Zhang, Bowen
    Davies, Huw M. L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (12) : 4937 - 4941
  • [4] Rhodium-catalyzed asymmetric [4+2] cycloisomerization reactions
    Gilbertson, SR
    Hoge, GS
    Genov, DG
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26): : 10077 - 10080
  • [5] Rhodium catalyzed intramolecular [4+2] cycloisomerization reactions
    Gilbertson, SR
    Hoge, GS
    TETRAHEDRON LETTERS, 1998, 39 (15) : 2075 - 2078
  • [6] Rhodium catalyzed intramolecular [4+2] cycloisomerization reactions
    Gilbertson, S. R.
    Hoge, G. S.
    Tetrahedron Letters, 39 (15):
  • [7] Theoretical elucidation of the rhodium-catalyzed [4+2] annulation reactions
    Geng, Cai-Yun
    Li, Ji-Lai
    Huang, Xu-Ri
    Liu, Hui-Ling
    Ll, Zhuo
    Sun, Chia-Chung
    JOURNAL OF COMPUTATIONAL CHEMISTRY, 2008, 29 (05) : 686 - 693
  • [8] Rhodium-catalyzed intermolecular [4+2] cycloaddition of unactivated substrates
    Murakami, M
    Ubukata, M
    Itami, K
    Ito, Y
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (16) : 2248 - 2250
  • [9] Highly enantioselective rhodium-catalyzed [4+2] annulation reactions
    Tanaka, Ken
    CHIMICA OGGI-CHEMISTRY TODAY, 2006, 24 (04) : 20 - +
  • [10] Mechanistic investigation of a rhodium-catalyzed [4+2] cycloaddition.
    Morehead, AT
    Kundu, K
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U130 - U130
12345