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
[1]   Expedient Synthesis of Phenanthrenes via In(III)-Catalyzed 6-Exo-Dig Cycloisomerization [J].
Kwon, Yongseok ;
Cho, Hyunkyung ;
Kim, Sanghee .
ORGANIC LETTERS, 2013, 15 (04) :920-923
[2]   Gold(I)-Catalyzed 6-exo-dig Hydroamination/7-endo-dig Cycloisomerization Domino Approach to 3,7a-Diazacyclohepta[jk]fluorene Derivatives [J].
Yang, Lu ;
Xie, Fukai ;
Zhang, Lianjie ;
Wei, Jipeng ;
Li, Jiaji ;
Li, Xiang ;
Fu, Jiayue ;
Lin, Bin ;
Cheng, Maosheng ;
Liu, Yongxiang .
ORGANIC LETTERS, 2024, 26 (46) :10030-10035
[3]   A Base-Mediated 6-exo-trig versus 6-exo-dig Carbocyclization Strategy for the Synthesis of Functionalized Biaryl Compounds [J].
Yadav, Pratik ;
Shaw, Ranjay ;
Panwar, Rahul ;
Sahu, Satya Narayan ;
Kumar, Abhinav ;
Pratap, Ramendra .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (10) :1394-1397
[4]   Mechanism of Gold-Catalyzed Cycloisomerization of Enynyl Esters [J].
Correa, Andrea ;
Cavallo, Luigi .
GREEN METATHESIS CHEMISTRY: GREAT CHALLENGES IN SYNTHESIS, CATALYSIS AND NANOTECHNOLOGY, 2010, :293-303
[5]   Gold-Catalyzed Cycloisomerization Reactions of 2-Tosylaminophenylprop-1-yn-3-ols as a Versatile Approach for Indole Synthesis [J].
Kothandaraman, Prasath ;
Rao, Weidong ;
Foo, Shi Jia ;
Chan, Philip Wai Hong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (27) :4619-4623
[6]   Gold-Catalyzed Cycloisomerization of Cyclopropyl Alkynyl Acetates: A Versatile Approach to 5-, 6-, and 7-Membered Carbocycles [J].
Zou, Yue ;
Garayalde, David ;
Wang, Quanrui ;
Nevado, Cristina ;
Goeke, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (52) :10110-10113
[7]   Gold-catalyzed 5-exo-dig and 6-exo-dig selective cyclizations of alkynyl silyl enol ethers:: Efficient method for [3+2] and [4+2] annulations onto α,β-enones [J].
Lee, Kooyeon ;
Lee, Phil Ho .
ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (13) :2092-2096
[8]   Mechanistic Insights into the Post-Cyclization Isomerization in Gold-Catalyzed 7-exo-dig-Hydroarylations [J].
Pflaesterer, Daniel ;
Schumacher, Soeren ;
Rudolph, Matthias ;
Hashmi, A. Stephen K. .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) :11585-11589
[9]   Gold-Catalyzed Tandem Cycloisomerization-Halogenation of Chiral Homopropargyl Sulfonamides [J].
Shu, Chao ;
Li, Long ;
Shen, Cang-Hai ;
Ruan, Peng-Peng ;
Liu, Chao-Yue ;
Ye, Long-Wu .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (07) :2282-2290
[10]   Gold-Catalyzed Approach to Multisubstituted Fulvenes via Cycloisomerization of Furan/Ynes [J].
Chen, Yifeng ;
Liu, Yuanhong .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (13) :5274-5282
12345