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

页码：1525 / 1529

页数：5

共 50 条

[41] Gold-catalyzed formation of substituted aminobenzophenone derivatives via intramolecular 6-endo-dig cyclization [J].

Dalovai, Purnachandar ;

Karunakar, Galla Venkata ;

Nadar, Vidya Damodaran ;

Doddi, Venkata Ramana ;

Kanaparthy, Suneel .

JOURNAL OF CHEMICAL SCIENCES, 2021, 133 (01)

[42] A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals [J].

Tlais, Sami F. ;

Dudley, Gregory B. .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :570-577

[43] Ammonium-Salt-Tagged IMesAuCl Complexes and Their Application in Gold-Catalyzed Cycloisomerization Reactions in Water [J].

Belger, Katrin ;

Krause, Norbert .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (01) :220-225

[44] Gold-Catalyzed One-Pot Cycloisomerization/Nucleophilic Addition/Rearrangement of Acenaphthylene Carbaldehyde Derivatives [J].

Truchon, Alexis ;

Dupeux, Aurelien ;

Olivero, Sandra ;

Michelet, Veronique .

ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (12) :2006-2012

[45] Poly(ethylene glycol) as a Reaction Matrix in Platinum- or Gold-Catalyzed Cycloisomerization: A Mechanistic Investigation [J].

Spina, Rosella ;

Colacino, Evelina ;

Martinez, Jean ;

Lamaty, Frederic .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (12) :3817-3821

[46] NHC-Stabilized Gold(I) Complexes: Suitable Catalysts for 6-exo-dig Heterocyclization of 1-(o-Ethynylaryl)ureas [J].

Gimeno, Ana ;

Medio-Simon, Mercedes ;

Ramirez de Arellano, Carmen ;

Asensio, Gregorio ;

Cuenca, Ana B. .

ORGANIC LETTERS, 2010, 12 (09) :1900-1903

[47] 6-Exo-dig cyclization/dearomatization cascade towards N-O fused spiro polyheterocycles [J].

Lv, Zhenwei ;

Li, Yan ;

Van der Eycken, Erik V. ;

Cai, Lingchao ;

Song, Liangliang .

ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (19) :4912-4917

[48] Gold-Catalyzed Diastereoselective Cycloisomerization of Alkylidene-Cyclopropane-Bearing 1,6-Diynes [J].

Zheng, Hongchao ;

Adduci, Laura L. ;

Felix, Ryan J. ;

Gagne, Michel R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (30) :7904-7907

[49] A convenient synthesis of pyrrolopyridines and 2-substituted indoles by gold-catalyzed cycloisomerization [J].

Majumdar, K. C. ;

Samanta, S. ;

Chattopadhyay, B. .

TETRAHEDRON LETTERS, 2008, 49 (50) :7213-7216

[50] When Gold Meets Perfumes: Synthesis of Olfactive Compounds via Gold-Catalyzed Cycloisomerization Reactions [J].

Laher, Romain ;

Marin, Christophe ;

Michelet, Veronique .

ORGANIC LETTERS, 2020, 22 (11) :4058-4062

← 1 2 3 4 5 →