Gold-Catalyzed 6-Exo-Dig Cycloisomerization: A Versatile Approach to Functionalized Phenanthrenes

被引：31
|
作者：
Shu, Chao [1 ,2 ]
Li, Long [1 ,2 ]
Chen, Cheng-Bin [1 ,2 ]
Shen, Hong-Cheng [1 ,2 ]
Ye, Long-Wu [1 ,2 ]
机构：
[1] Xiamen Univ, State Key Lab Phys Chem Solid Surfaces, Key Lab Chem Biol Fujian Prov, Xiamen 361005, Fujian, Peoples R China
[2] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China
来源：
CHEMISTRY-AN ASIAN JOURNAL | 2014年 / 9卷 / 06期
基金：
中国国家自然科学基金;
关键词：
cycloisomerization; gold; homogeneous catalysis; hydroarylation; phenanthrenes; POLYCYCLIC AROMATIC-HYDROCARBONS; ONE-POT SYNTHESIS; HYDROARYLATION REACTIONS; PHOTOPHYSICAL PROPERTIES; OXIDATIVE CYCLIZATION; CARBENE COMPLEXES; ALKYNES; CRYPTOPLEURINE; CONSTRUCTION; (-)-ANTOFINE;
D O I：
10.1002/asia.201400034
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel gold-catalyzed 6-exo-dig cycloisomerization of o-propargylbiaryls has been developed that provides ready access to functionalized phenanthrenes in largely good to excellent yields. Notable features of this method are readily available starting materials, mild reaction conditions, and broad substrate scope.
引用
收藏
页码：1525 / 1529
页数：5
相关论文
共 50 条
  • [21] Synthesis of functionalized carbo- and heterocycles via gold-catalyzed cycloisomerization reactions of enynes
    Leseurre, Lucie
    Chao, Chung-Meng
    Seki, Tomohiro
    Genin, Emilie
    Toullec, Patrick Y.
    Genet, Jean-Pierre
    Michelet, Veronique
    TETRAHEDRON, 2009, 65 (09) : 1911 - 1918
  • [22] 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
  • [23] Gold-Catalyzed Cycloisomerization Reactions of 2-Tosylaminophenylprop-1-yn-3-ols as a Versatile Approach for Indole Synthesis
    Kothandaraman, Prasath
    Rao, Weidong
    Foo, Shi Jia
    Chan, Philip Wai Hong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (27) : 4619 - 4623
  • [24] Access to 1,4-Thiazepanes via Gold-Catalyzed 7-exo-dig Thioallylation and their Cycloisomerization to Bicyclic [4.3.1] Bridgehead-Olefinic Systems
    Choury, Mickael
    Wagner, Patrick
    Rognan, Charlou
    Blond, Gaelle
    Gulea, Mihaela
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (18) : 3238 - 3244
  • [25] The influence of electronic factors on Pd-mediated cycloisomerization: a systematic investigation of competitive 6-exo-dig versus 7-endo-dig cyclizations of sugar alkynols
    Ramana, C. V.
    Induvadana, Boddeti
    Srinivas, Burgula
    Yadagiri, Kommagalla
    Deshmukh, Madhusudhan N.
    Gonnade, Rajesh G.
    TETRAHEDRON, 2009, 65 (47) : 9819 - 9832
  • [26] RING-CLOSURE TO YNONE SYSTEMS - 5-ENDO-DIG AND 6-ENDO-DIG AND 6-EXO-DIG MODES
    BRENNAN, CM
    JOHNSON, CD
    MCDONNELL, PD
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (08): : 957 - 961
  • [27] Mechanistic Insights into the Post-Cyclization Isomerization in Gold-Catalyzed 7-exo-dig-Hydroarylations
    Pflaesterer, Daniel
    Schumacher, Soeren
    Rudolph, Matthias
    Hashmi, A. Stephen K.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) : 11585 - 11589
  • [28] Gold-catalyzed cycloisomerization of enynamides: Regio- and stereoselective approach to tetracyclic spiroindolines
    Zhu, Baolong
    Zhu, Lei
    Xia, Jiajin
    Huang, Shenlin
    Huang, Xueliang
    TETRAHEDRON, 2020, 76 (51)
  • [29] On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions
    Fuerstner, Alois
    Morency, Louis
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (27) : 5030 - 5033
  • [30] Gold-catalyzed alkyne cycloisomerization strategies in heterocyclic synthesis
    Chan, Philip Wai Hong
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
12345