Gold-Catalyzed Benzannulation of 3-Alkoxy-1,5-enynes: Access to Functionalized Benzenes

被引:17
|
作者
Li, Guijie [1 ]
Liu, Yuanhong [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 09期
基金
中国国家自然科学基金;
关键词
HIGHLY EFFICIENT SYNTHESIS; AROMATIC ENYNES; CYCLIZATION; CYCLOISOMERIZATION; PLATINUM; HYDROXYCYCLIZATION; ALKOXYCYCLIZATION; ALKYNES; HETEROCYCLES; CARBOCYCLES;
D O I
10.1021/jo100137j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cationic Au(I) complex catalyzed benzannulation of 3-alkoxy-1,5-enynes bridged by a cyclopropyl ring with a variety of nucleophiles is described. The reaction occurs selectively through a 6-endo-dig pathway to provide tri- and tetrasubstituted benzenes efficiently under mild reaction conditions.
引用
收藏
页码:2903 / 2909
页数:7
相关论文
共 50 条
  • [1] Gold-Catalyzed Cycloisomerization of Functionalized 1,5-Enynes - An Entry to Polycyclic Framework
    Pradal, Alexandre
    Chen, Qian
    Bel, Pierre Faudot Dit
    Toullec, Patrick Yves
    Michelet, Veronique
    SYNLETT, 2012, 23 (01) : 74 - 79
  • [2] Gold-Catalyzed Cyclization of Oxo-1,5-enynes
    Huguet, Nuria
    Echavarren, Antonio M.
    SYNLETT, 2012, 23 (01) : 49 - 53
  • [3] DFT Studies on Gold-Catalyzed Cycloisomerization of 1,5-Enynes
    Fan, Ting
    Chen, Xihan
    Sun, Jianwei
    Lin, Zhenyang
    ORGANOMETALLICS, 2012, 31 (11) : 4221 - 4227
  • [4] Gold-Catalyzed Oxidative Cyclization of 1,5-Enynes Using External Oxidants
    Vasu, Dhananjayan
    Hung, Hsiao-Hua
    Bhunia, Sabyasachi
    Gawade, Sagar Ashok
    Das, Arindam
    Liu, Rai-Shung
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (30) : 6911 - 6914
  • [5] Mimicking Polyolefin Carbocyclization Reactions: Gold-Catalyzed Intramolecular Phenoxycyclization of 1,5-Enynes
    Toullec, Patrick Yves
    Blarre, Thomas
    Michelet, Veronique
    ORGANIC LETTERS, 2009, 11 (13) : 2888 - 2891
  • [6] Gold(I)-catalyzed benzannulation of 3-hydroxy-1,5-enynes:: an efficient synthesis of substituted tetrahydronaphthalenes and related compounds
    Grise, Christiane M.
    Rodrigue, Eric M.
    Barriault, Louis
    TETRAHEDRON, 2008, 64 (05) : 797 - 808
  • [7] Gold-Catalyzed Enantioselective Ring-Expanding Cycloisomerization of Cyclopropylidene Bearing 1,5-Enynes
    Zheng, Hongchao
    Felix, Ryan J.
    Gagne, Michel R.
    ORGANIC LETTERS, 2014, 16 (08) : 2272 - 2275
  • [8] Gold(I)-catalyzed dehydrogenative cycloisomerization of 1,5-enynes
    Chen, Gen-Qiang
    Fang, Wei
    Wei, Yin
    Tang, Xiang-Ying
    Shi, Min
    CHEMICAL COMMUNICATIONS, 2016, 52 (71) : 10799 - 10802
  • [9] Gold-catalyzed reactivity of 3-silyloxy-1,5-enynes: a synthetic tool for the synthesis of complex structures and its limitations
    Menz, Helge
    Binder, Joerg T.
    Crone, Benedikt
    Duschek, Alexander
    Haug, Timm T.
    Kirsch, Stefan F.
    Klahn, Philipp
    Liebert, Clemence
    TETRAHEDRON, 2009, 65 (09) : 1880 - 1888
  • [10] Gold-Catalyzed Cyclization/Oxidative [3+2]Cycloadditions of 1,5-Enynes with Nitrosobenzenes without Additional Oxidants
    Chen, Chun-Hao
    Tsai, Yen-Ching
    Liu, Rai-Shung
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (17) : 4599 - 4603