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
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
  • [21] Synthesis of novel hydronaphthalenes via a rhodium-catalyzed [4+2] cycloaddition.
    Morehead, AT
    McCullagh, JV
    Pancost, MR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U153 - U153
  • [22] Enantioselective synthesis of spirocyclic benzopyranones by rhodium-catalyzed intermolecular [4+2] annulation
    Hojo, Daiki
    Noguchi, Keiichi
    Hirano, Masao
    Tanaka, Ken
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (31) : 5820 - 5822
  • [23] Rhodium-Catalyzed Regioselective [4+2] Cycloaddition of Ynamines and 2-(Cyanomethyl)phenylboronates
    Xie, Zhong-Yang
    Tang, Conghui
    Li, Long
    Zhou, Zijun
    Zou, Jun
    Qian, Peng-Cheng
    ORGANIC LETTERS, 2024, 26 (31) : 6586 - 6590
  • [24] Rhodium-catalyzed intramolecular hydrosilylation of allenes
    Commandeur, C
    Varchi, G
    Shimizu, K
    Ojima, I
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3248 - U3249
  • [25] Rhodium-catalyzed intramolecular alkynylsilylation of alkynes
    Shintani, Ryo
    Kurata, Hiroki
    Nozaki, Kyoko
    CHEMICAL COMMUNICATIONS, 2015, 51 (57) : 11378 - 11381
  • [26] Rhodium-catalyzed intramolecular silylformylation of alkenes
    Leighton, JL
    Chapman, E
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12416 - 12417
  • [27] Transition metal-catalyzed intramolecular [4+2] cycloadditions: Mechanistic and synthetic investigations
    Wender, PA
    Smith, TE
    TETRAHEDRON, 1998, 54 (07) : 1255 - 1275
  • [28] INTRAMOLECULAR (4+2)-CYCLOADDITIONS WITH INVERTED ELECTRON REQUIREMENTS
    SCHUSTER, H
    SAUER, J
    TETRAHEDRON LETTERS, 1983, 24 (38) : 4087 - 4090
  • [29] Enantioselective Helicene Synthesis by Rhodium-Catalyzed [2+2+2] Cycloadditions
    Tanaka, Ken
    Kimura, Yuki
    Murayama, Koichi
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (03) : 375 - 385
  • [30] Chiral alkynamides as substrates for intramolecular [4+2] cycloadditions
    Mulcahy, Seann P.
    Thomas, Stacy K.
    Giulietti, Jennifer M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245