Gold-Catalyzed Intramolecular Indole/Alkyne Cyclization Cascades through a Heterolytic Fragmentation: 1,5-Indole Migration and Allenylation

被引：40

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 / 10期

基金：

中国国家自然科学基金;

关键词：

INTERMOLECULAR REACTIONS; INDOLES; CYCLOISOMERIZATIONS; PLATINUM; ALLENES; ALKYNES; CARBON;

D O I：

10.1021/jo1005125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Gold-catalyzed intramolecular reactions of 3-alkynyl-bearing indoles with diol groups lead to the formation of highly functionalized 3-allenylindoles with high efficiency. The reaction likely proceeds by a new gold-catalyzed cascade cyclization/heterolytic fragmentation/elimination reactions, which results in 1,5-indole migration and C-3 allenylation of indole moiety.

引用

页码：3526 / 3528

页数：3

共 38 条

[1] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[2] Uncommon intramolecular palladium-catalyzed cyclization of indole derivatives [J].

Beccalli, EM ;

Broggini, G .

TETRAHEDRON LETTERS, 2003, 44 (09) :1919-1921

[3] Silver and Gold Catalysis for Cycloisomerization Reactions [J].

Belmont, Philippe ;

Parker, Evelyne .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (35) :6075-6089

[4] A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction [J].

Bressy, C ;

Alberico, D ;

Lautens, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13148-13149

[5] Gold-Catalyzed Cascade Friedel-Crafts/Furan-Alkyne Cycloisomerizations for the Highly Efficient Synthesis of Arylated (Z)-Enones or -Enals [J].

Chen, Yifeng ;

Lu, Yuhua ;

Li, Guijie ;

Liu, Yuanhong .

ORGANIC LETTERS, 2009, 11 (17) :3838-3841

[6] Efficient Synthesis of the Indoloazocine Framework via Intramolecular Alkyne Carbocyclization [J].

Donets, Pavel A. ;

Van Hecke, Kristof ;

Van Meervelt, Luc ;

Van der Eycken, Erik V. .

ORGANIC LETTERS, 2009, 11 (16) :3618-3621

[7] Gold-catalyzed cycloisomerization of N-propargylindole-2-carboxamides:: Application toward the synthesis of lavendamycin analogues [J].

England, Dylan B. ;

Padwa, Albert .

ORGANIC LETTERS, 2008, 10 (16) :3631-3634

[8] Gold-catalyzed intramolecular reaction of indoles with alkynes: Facile formation of eight-membered rings and an unexpected allenylation [J].

Ferrer, C ;

Echavarren, AM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (07) :1105-1109

[9] Intra- and intermolecular reactions of indoles with alkynes catalyzed by gold [J].

Ferrer, Catalina ;

Amijs, Catelijne H. M. ;

Echavarren, Antonio M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (05) :1358-1373

[10] Synthesis of the tetracyclic core skeleton of the lundurines by a gold-catalyzed cyclization [J].

Ferrer, Catalina ;

Escribano-Cuesta, Ana ;

Echavarren, Antonio M. .

TETRAHEDRON, 2009, 65 (44) :9015-9020

← 1 2 3 4 →